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Saturday, December 12, 2015, marks what would have been Frank Sinatra’s 100th birthday. Born in Hoboken, New Jersey, in 1915, he rose from humble beginnings to become the greatest entertainer of the twentieth century. Anyone who delves into the so-called “Great American Songbook” owes a debt to Sinatra. He didn’t write the songs, but he used the force of his voice and his powerful personality to make them his own.

As a human being, though, to say that Sinatra was “flawed” is a bit of an understatement. He contained multitudes. He was tough and tender, mean and romantic, loyal and unforgiving, good and bad. He could turn his emotions up to 11 at the drop of a snap-brimmed hat, and there are many stories of one-time friends who crossed Sinatra and earned his everlasting hatred.

But with Sinatra, you have to take the good with the bad. It’s like the episode of “Star Trek” where the transporter splits the captain into two people: good Kirk and bad Kirk. Bad Kirk is a total dick. Good Kirk is a nice guy, but he lacks the balls to make the tough decisions a captain has to make. To be an effective commander, Kirk needs both sides of his personality.

Sinatra was like that. He was a smoldering cauldron of emotions: resentment, anger, envy, loneliness. He could also be incredibly giving, although always on his own terms. When the volcano inside him erupted in his ordinary life, the results were often not pretty. When he channeled that intense emotional life into his singing, the results could be transcendent. His artistry came with a price.

I can vividly remember when I became a Frank Sinatra fan. I was attending college in Los Angeles, living in an old apartment building on Vermont Avenue. My tiny room smelled of leaking gas and roach powder.

Shabby as it was, the place had its strong points. Right across from the front entrance was Benjy’s Liquor, and Benjy never carded. And the building had a big expansive roof, where I could sit on a late afternoon, watch the sun set over Los Angeles, drink the beer I had bought at Benjy’s, and listen to KROQ.

KROQ was Los Angeles’ “new wave” station. It played artists like the Plimsouls, XTC, Sparks, and Split Enz. It was not in the habit of playing Frank Sinatra. Yet one evening I was sitting on the roof, drinking a beer as the setting sun turned the sky the color of an orange popsicle, and the DJ played a song I recognized from my youth—the title track to Come Fly with Me. My Dad had the album. The song was brassy and upbeat, with muted trumpets kicking things off, and Frank singing about heading off to “llama land, where a one-man band, will toot his flute for you.” It hovered just the right side of self-parody. It also made me feel good hearing it. The next day I headed off to the used record stores on Fairfax Avenue and I bought a copy of the album. I still have it.

That was the beginning of my Sinatra fandom. The next album I bought was Sinatra’s Swingin’ Session!!!, an album so swingtastic it required three exclamation points in its title. I found out later that this was the last album Sinatra had done for Capitol Records. The story goes that Sinatra walked into the studio and told arranger Nelson Riddle to pick up the tempo for all the numbers, without even hearing them. The album does have a rollicking pace, and the original vinyl version clocks in at less than 30 minutes. It does swing, though.

After graduating from college I returned to the East Coast, and I began dipping into my dad’s Sinatra albums. He had a copy of A Swingin’ Affair!, another great collaboration with Riddle. Some friends of my parents had left it behind after a party. (Their name was still written on the album.) Once I moved to Boston, I started buying more albums. One of the first was a collection called This is Sinatra!, which introduced me to the brassy charms of “I’ve Got the World on a String,” still one of my favorite Sinatra songs, and one of the first collaborations with Riddle.

I also bought a copy of Songs for Swingin’ Lovers! It was one of the cheap reissues that Capitol released in the early 1980s. I didn’t find out until years later that the label dropped songs from these new versions to save money, probably to make pressing them cheaper. Songs for Swingin’ Lovers! originally had 15 tracks. Mine had a mere dozen. Among the missing were “Pennies from Heaven” and “Makin’ Whoopee.” Even shortened, the album worked. The first time my future wife visited my apartment, I threw Swingin’ Lovers on the turntable. She was impressed by my savoir faire, or whatever it was. When we got married, our first song was Sinatra’s version of “More.”

All of which is a long way to say, happy birthday, Frank.

I wrote the following piece as part of a book proposal that never got off the ground. I thought the occasion of Sinatra’s 100th would be a good time to share it.

“He’s hot, he’s sexy, and he’s dead.”

Rolling Stone once used that line for a cover story about Jim Morrison. They could use it today to describe Frank Sinatra. Since his death in 1998, the legendary vocalist has appeared in slick ads for Jack Daniels. He provided the soundtrack (and the style) for vodka ads featuring Sean “Diddy” Coombs. He has become an avatar of cool for the hip-hop generation, the Original Gangsta. HBO recently ran a two-part series about Sinatra, part of the build-up to the commemoration of what would have been Sinatra’s 100th birthday on December 12, 2015.

“Frank Sinatra was the 20th century,” said Bono, vocalist for U2, when he saluted the still-living legend in 1994. “He was modern; he was complex; he had swing and attitude. He was the big bang of pop.” Bono knew what he was talking about. Sinatra is arguably the greatest entertainer of the 20th century. Yet he came dangerously close to becoming little more than a footnote in musical history, just one of the strange fads that appeared during World War II. During late 1940s and early 1950s, Sinatra watched his career disintegrate. His label and movie studio dropped him, his audiences grew up and stayed home, and his voice failed. It could all have ended then, not with some swing but with a whimper, and we would have never heard Sinatra’s work with Nelson Riddle, or great albums like Songs for Swingin’ Lovers!

Fortunately for Sinatra and for musical history, Capitol Records came calling. Even more important, the label decided to pair Sinatra with arranger Nelson Riddle. On the surface, the two men seemed remarkably similar. Both hailed from New Jersey, the only children of dominating mothers. Both emerged from the big band era and spent time with Tommy Dorsey’s band. In reality, though, Sinatra/Riddle was an unlikely pairing. Sinatra was—well, Frank Sinatra. He was a hot-tempered boozer and brawler who wore his nerves on his sleeve. Riddle was more subdued (although he did father a child out of wedlock with singer Rosemary Clooney). He was quiet, brooding and introspective, with a sardonic sense of humor produced during a grim childhood. “We didn’t feel the Depression at all, because my father created his own Depression,” he once said. “It was all the same to us because we were already in a depressed state by the time the Depression got there.” Riddle was also a musical genius with a knack for surrounding vocalists with artful, playful arrangements. By the time Capitol teamed him with Sinatra, Riddle had already had arranged hits for Nat King Cole and others, but he found his greatest musical collaborator in Sinatra. “The man himself somehow draws everything out of you,” Riddle once said. “And I always felt that my rather placid disposition had a beneficial effect on him. I was able to calm him down sometimes. He would start snapping at somebody and I would say, ‘Come on, pal, what’s the point of doing that?’ He’d give me a hard look, then he’d stop.”

Riddle never became part of Sinatra’s high-living Rat Pack, but he played a central role in the singer’s life. He helped create Sinatra forge a signature sound that defined, in its way, a portion of the mid-twentieth century. Their collaboration created “one of the greatest bodies of music in all of American popular culture,” wrote musicologist Will Friedwald in his book about Sinatra’s recordings. “In truth virtually all the Sinatra-Riddle albums are masterpieces, their collaboration being sanctified from the first downbeat counted off at the first session onward.”

And it almost never happened.

Frank Sinatra was fast approaching rock bottom when he went out on the stage at the Copacabana for the last show on April 26, 1950.

The bobby soxers who had shrieked for Frankie were long gone. George Evans, the press agent whose behind-the-scenes manipulation of those bobby soxers had helped turn Frankie into the biggest thing in music, had died back in January. Frank’s marriage to wife Nancy, strained after years of infidelities, finally blew following the revelations of his affair with actress Ava Gardner. His record sales were in free fall. MGM’s Louis B. Mayer had dumped him.

Things got even worse for the Voice at the Copa. Sometime around 2:00 a.m. that morning, Sinatra approached the mike to start his final show of the night. He opened his mouth to sing—and nothing came out. “Just dust,” he said. The small audience stared at Sinatra. Sinatra stared back at them. “I was never so panic-stricken in my life,” he said. Finally, the singer managed to whisper “Good night” and walked offstage.

It hadn’t been so long since Frank Sinatra had been on top of the world. He had come a long way from Hoboken, where he was the only son of a force of nature named Dolly Sinatra and Antony Martin Sinatra, her sometimes dock worker/bartender/boxer husband. Born in Hoboken on December 12, 1915, Francis Albert Sinatra decided at an early age he wanted to be a singer. The story goes that he attended a Bing Crosby show one night and told his girlfriend (and future wife) Nancy Barbato, “Someday that will be me up there.” He sang and toured with a local trio that made a splash on the Major Bowes Amateur Hour as the Hoboken four, but he got his big break as a singing waiter at the Rustic Cabin, a roadhouse in Englewood, New Jersey. One night trumpeter and bandleader Harry James came in to size up the local talent. “He’d sung only eight bars when I felt the hairs on the back of my neck rising,” James recollected about the first time he heard Sinatra. “I knew he was destined to be a great vocalist.” Sinatra signed with James in February 1939, at $75 a week.

He didn’t stay with James for long. By the end of the year he was aiming higher—at Tommy Dorsey, leader of the number one band in the country. In January 1940 Sinatra left the struggling James band—Harry tore up the contract—and signed with Dorsey for $125 week. The next year Billboard picked Sinatra as the nation’s top vocalist. He learned a lot from Dorsey, most notably by watching how the bandleader played his trombone, especially how he controlled his breathing to create the smooth legato for which he was known. “He would take a musical phrase and play it all the way through seemingly without breathing for 8, 10, maybe 16 bars,” Sinatra said in an article for Life magazine in 1965. “Why couldn’t a singer do that, too?” he wondered. Sinatra also listened to the violin playing of Jascha Heifetz, the way the violinist played without taking a break in the melody line. “It was my idea to make my voice work in the same way as a trombone or a violin—not sounding like them, but ‘playing’ the voice like those instruments.”

Another thing Sinatra learned was the value of the microphone. “Many singers never learned to use one,” he said. “They never understood, and still don’t, that a microphone is their instrument.” Sinatra understood that perfectly well, and had a keen sense of the way amplification offered the singer an almost intimate bond with the listener.

But although Sinatra owed a lot to Dorsey, it wasn’t long before he was straining at the leash. Dorsey may have been known as “the Sentimental Gentleman of Swing,” but in reality he was a tough-as-nails taskmaster with an explosive temper. Long before Sinatra’s three-year contract was up, the ambitious singer decided he wanted to strike out on his own. One motivation was an overture by Manie Sacks of Columbia Records, who encouraged Sinatra to record solo for his label. Unlike James, Dorsey wasn’t quite so willing to tear up a contract. He insisted on extracting plenty of cash in exchange for Sinatra’s freedom. The deal sparked rumors that the mob had played a role (as portrayed in fictionalized form in The Godfather), and it left a good deal of bitterness behind. “I hope you fall on your ass,” Dorsey told his now ex-singer.

Dorsey got his wish, but it took almost a decade for it to happen. First, Sinatra ascended to dizzying heights of fame and adulation, starting with a gig opening for the Benny Goodman band at New York’s Paramount Theater on December 20, 1942. By then the young women known as bobby soxers had embraced the young Sinatra with an emotional frenzy. Something about the strangely vulnerable (on stage, anyway), skinny young man with the oversized bow ties, the aching voice and the blue eyes set them ablaze. His gig at the Paramount became a sensation. Singer Peggy Lee said there was something “electric” when Sinatra came on stage. “We used to lean out the windows of the dressing room to see the crowd of swooners, like swarms of bees down there in the street, just waiting for the sight of Frankie,” she said.

Sinatra’s press agent, George Evans, claimed some of the credit, saying he paid bobby soxers to swoon and cause a scene. But anyone could see that Sinatra’s appeal was more than just flackery. Young women screamed his name, mobbed him, and nearly strangled him when they grabbed at his bow ties. His voice was full of yearning; they yearned for him. Sinatramania grew and grew, as he hosted Your Hit Parade on radio and appeared in films and on stage. Sinatra, who had a perforated eardrum that kept him from being drafted, attributed some of the hysteria to his role as the stand-in for all the young men who were overseas.

Sinatra signed with Columbia Records in 1943, but a musicians’ strike kept him from recording new material with a band. To get around the strike, Sinatra recorded some a Capella records and even charted a hit single with the re-release of the Harry James version of “All or Nothing at All.” When the recording ban finally ended 1944, Sinatra embarked on his first great musical partnership, with arranger/conductor Axel Stordahl. The two had met in Dorsey’s band, where Stordahl did some arranging. The bald, pipe-smoking, tweed-wearing Stordahl looked like a music professor, and he wrapped Sinatra’s voice in almost classical arrangements. John Rockwell described the recordings they did together as “a wash of strings and lush, neo-Tchaikovskian arrangements to accompany Sinatra’s gorgeous, lyrical, intimate, introspective ballad singing.” On the strength of his work with Stordahl, Sinatra earned the nickname of “The Voice.” But, let’s face it; those recordings were a little boring.

The bobby soxers who swarmed his live performances were anything but bored. Things peaked in October 1944 and the “Columbus Day Riots. Sinatra was booked for a return engagement at New York’s Paramount Theater, the same venue where he had launched his solo career. On October 11, a school holiday, the bobby soxers were waiting for him in droves, perhaps as many as 10,000, standing in long lines that stretched down the street and around the block. Trouble broke out when the fans inside for the first show refused to give up their seats for those waiting outside.

“For Sinatra that stand at the Paramount was a kind of culmination, the final explosive orgy of his cult of youth,” wrote James Kaplan in his 2010 biography. He was still popular, but he had apparently peaked. His young followers were growing up. The war was ending, and a resumption of normal life beckoned.

Sinatra did what he could to hasten his decline. More and more he became a topic in gossip columns—if he wasn’t slugging newspaper columnists, he was squiring women not his wife around town. It was not good for his image. His very public affair with smoldering actress Ava Gardner finally put an end to his marriage with Nancy, while his left-leaning politics caught the attention of the FBI.

The musical front was just as rocky. In 1950, producer Mitch Miller took over as chief of recording at Columbia Records. Miller’s work with Sinatra would mark the nadir of the singer’s career, culminating with the now infamous “Mama Will Bark,” in which Sinatra shared vocal duties with the Swedish model Dagmar and a man howling like a dog. (Of Miller, Sinatra biographer John Rockwell wrote, “His taste was so silly that he seems in retrospect to have been placed on this planet for the express purpose of heralding rock’s cleansing passion.”) Miller’s arrival at Columbia’s helm was the beginning of the end for Sinatra’s stint at the label. He and Columbia finally parted ways in 1952.

Things were about to get better.

Capitol Records was founded in 1942 by two songwriters—Johnny Mercer and Buddy DeSylva—and one record store owner—Glenn Wallichs, who owned Music City in Hollywood.

Financed by $25,000 of Mercer’s money, the fledgling label managed to survive the war years despite a lack of shellac to make records and the recording ban that had also hobbled Sinatra’s start with Columbia. By the time Sinatra signed in 1953, Capitol was going strong.

A lot of people took credit for getting Sinatra to his new label. Singer Jo Stafford, who recorded for Capitol, said she suggested to Dave Dexter, Jr., a producer at Capitol, that he sign Sinatra. Dexter went to see Sinatra perform, was sufficiently impressed by what he heard (the singer had bounced back from his throat woes), and gave the label a favorable report.

Alan Livingston, Capitol’s A&R vice president, remembered it differently. Livingston said he received a call from Sinatra’s new agent, Sam Weisbord of William Morris, to see if Capitol was interested. “Sinatra had hit bottom, and I mean bottom,” Livingston recalled for author Charles L. Granata. “He couldn’t get a record contract, and he literally, at that point, could not get a booking in a nightclub. It was that bad—he was broke, and in a terrible state of mind.”

Livingston signed him anyway.

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GoldfingerDuring today’s walk the iPod segued from Shirley Bassey doing the theme from Goldfinger to Frank Sinatra singing “Day in, Day out.” It made me think, as I often do, of a lost opportunity. I wish Sinatra had played Felix Leiter in the James Bond films.

Leiter, for all who don’t know this important fact, was 007’s CIA connection. The character appeared in several of Ian Fleming’s Bond novels, and also showed up in the movies—usually played by a different actor each time. Jack Lord was perfectly adequate in the role opposite Sean Connery’s Bond for the first film, Dr. No, but things went downhill from there. In Goldfinger, Leiter was played by charisma-challenged Canadian actor Cec Linder. Cec Linder! Suffice it to say, you can easily imagine Linder’s Leiter taking a break from his agency duties to peddle Fuller brushes door to door. In Thunderball, Leiter shows up in the guise of an actor named Rik Van Nutter. I’ve seen the movie several times and I can barely remember him.

But there is a parallel universe, one that’s just a little better than ours, where Sinatra did play Leiter. Here’s an excerpt from a film history published in that alternate universe:

“Sinatra had already provided the vocals for the title song for From Russia with Love, so an on-screen teaming with Connery for Goldfinger seemed like a natural fit. ‘Sinatra brings a tough, wolfish American quality to the character of CIA agent Felix Leiter, and he meshes perfectly with Connery’s suave British spy,’ wrote Arthur Knight in his review of Goldfinger for Saturday Review. Producers Cubby Broccoli and Harry Saltzman immediately signed Sinatra to reprise his role in Thunderball. Before shooting, the actors demanded script rewrites. “Haggis [Connery] and I both thought the gadgets had run their course,” Sinatra told an interviewer. “We wanted to get back to pure spy stuff, like the books.” The result was the leanest, tautest Bond yet. Connery was so pleased with the result, he insisted Sinatra receive a cameo in the next film, On Her Majesty’s Secret Service (considered by most Bond fans to be the best of the series), and then agreed to give Sinatra co-billing on Diamonds Are Forever, a gritty revenge thriller that unfolds in the shadows behind the bright lights of Las Vegas. Sinatra went on to play Leiter in three “Agency” films, with diminishing results. The first film, The Agency (with Connery taking a cameo as Bond) was generally well received, but the last in the series, Leiter’s Out! degenerated into a grab bag of Rat Pack shenanigans with everyone from Joey Bishop to Sammy Davis, Jr., showing up to join in the alleged fun.”

In this different and better parallel universe, Richard Castellano reprises his role as Clemenza for Godfather II and George Lucas decides that three Star Wars films are enough.

(For those wanting a complete Leiter list, here’s one from the Internet Movie Database.

Squeeze is singing “I’ve Returned.” In fact, it has been more than a week since I last headed out for a real walk, ever since Mother Nature delivered a nice one-two punch to stun the American northeast. In less than a week we received around three feet of snow here in central Pennsylvania. It just shows the wisdom of the saying, “Be careful what you wish for.” I love snow and have been saying all winter that we need some good storms, but the second blizzard ruined plans my family and I had to fly to San Diego for a few days. I had business there; they were going to have fun. Instead we’re all stuck here. We now have more snow than most of New England.

It’s a gray morning. The sun is pale and wan behind the overcast. Dog piss stains the snow banks, which are already starting to look as ragged and dirty as a hobo’s overcoat. I’m not in a particularly good mood. Not only did I miss out on a trip to California, I’m under a lot of pressure to finish a freelance project. The funny thing is, it involves the power of positive thinking. I’m not laughing.

The iPod must sense my mood, because it starts delivering energetic guitar-oriented songs that slowly begin lifting my spirits. I hear the Old 97s (“The Easy Way”) and Golden Smog (“To Call my Own”). Things really pick up with the Magic Numbers’ “Love Me Like You Do” from their great debut album. I first heard the band in a music video that came on a DVD in Paste magazine and I liked the song so much I bought the album. It’s wonderful melodic pop music with a cool interplay between male and female voices (two brother and sister pairs, from what I recall), like the Mammas and the Pappas updated for a new century.

Luna comes next with “Speedbumps” from their last album, Rendezvous. It’s another great song and also one I first heard via Paste. I had been a Luna fan before then, though. I was initially interested because of their  Feelies connection  (drummer Stan Demeski). In fact, I’ve spent a lot of time tracking down Feelies spinoffs, which include Yung Wu, Speed the Plough, and Wake Ooloo. A guy I knew in Baltimore was going to get me a copy of an EP by the Willies (or maybe it was the Trypes), but it was gone by the time he got back to the record store. I still regret that. Just recently I bought Glenn Mercer’s solo album, Wheels in Motion. It’s a pretty low-key affair, but I must admit to being impressed by his cover of “Within You, Without You,” George Harrison’s neo-Indian track from Sgt. Pepper. I always liked that song and Mercer does a nice job with it by merging it with Harrison’s “Love You To.”

But I digress. John Hiatt comes up next with “Georgia Rae” from Slow Turning as I carefully navigate the sometimes icy sidewalks.  I’ve seen Hiatt a bunch of times. One of the most memorable was when he played solo at the Barns at Wolftrap in Northern Virginia shortly before the release of his breakthrough album, Bring the Family. The peak moment came when he sat down at the piano and played a new song, “Have a Little Faith in Me,” that just floored us all. The gig was also memorable because a friend, who was godawful behind the wheel, drove my wife and me to it. As soon as he picked us up at the Metro he tried to make a U-turn and bumped over the median. For the rest of the trip he behaved like a man with at best a passing familiarity with motor vehicles. On the way back he kept following a big truck even as the rig pulled into the breakdown lane and stopped. My wife, who is a nervous passenger even in the best of times, was trying to stay calm by slugging back our drink of the night, a wicked mixture of Hawaiian punch and Southern Comfort. I don’t know how we came up with that. Fortunately we survived both the trip and the cocktail beverage. Good times.

Now Frank Sinatra sings “River Stay Away from my Door” and really gets me swingin’. The first time I ever heard this I was driving to Colonial Williamsburg for some business. I was somewhere in Virginia, searching across the radio dial around rush hour, when I stumbled across an all-Sinatra show. The song blew me away. It’s one of those great build-to-a-great climax songs with an arrangement by Nelson Riddle. I was finally able to add the song to my collection when I purchased a box set of all Sinatra’s singles from his years with Capitol.

I end the walk on a high note, with Matthew Sweet’s “Divine Intervention,” from the great Girlfriend album. Richard Lloyd provides some stinging, dirty guitar on this one.

Does He love us, does He love us, does He love us, does He love us?
Hmm, now does He love us?
 I look around
And all I see is destruction.
We’re all counting on His divine intervention.

 Man, when those guitars come ripping in it makes everything feel better. I love it when Sweet says, “Here it comes,” and chuckles, followed by a drum fill that announces, yes indeed, here it comes, and then it’s another onslaught of guitars that just sweep over me like a rock and roll tsunami. Turn it up to 11! By the time it’s over I feel like I’m ready to sit down at the computer and face some more positive thinking.

Swingin AffairAsk me what my favorite Frank Sinatra song is and I’ll probably say “I’ve Got You Under My Skin,” the version from Songs for Swingin’ Lovers. It’s an easy pick. The song’s a classic Cole Porter tune with a great Nelson Riddle arrangement. The Milt Bernhart trombone solo near the end kicks in like a musical afterburner to really give things a boot. Frank nails the vocal with the practiced ease of an artist at the top of his game. This is the Sinatra/ Riddle team working at its peak.

There are times, though, when I’ll tell you my favorite Sinatra song is one I heard as I walked this morning. “From This Moment On” is a cut from A Swingin’ Affair! It’s another Cole Porter song, and another superb Nelson Riddle arrangement. This one steps off nice ’n’ easy with some swirling flutes that lead into the vocal. Then things start to gradually build. The band picks up intensity, saxes and trumpets riffing off each other, trombones providing their own counterpoint, drums and bass pushing everything along, piano tinkling away in the background, and Frank just surfs along on top of the arrangement. The whole thing just sweeps you up and takes you along for the ride. Fingers feel an irresistible impulse to start snappin’. Near the end the rhythm section drops away and Frank and the horns keep things percolating for a few bars, and then everyone jumps back in for the finish. By this time I figure Frank had his eyes closed, head tilted back, arms stretched out, as he headed into the home stretch. Pure bliss. I sometimes think that if I could sing like that my life would be perfect. But Frank could sing like that, and he was a mess. So go figure.

I often see Songs for Swingin’ Lovers cited as Frank’s best work. For my money, A Swingin’ Affair! has it beat. The song choices are better overall, and the album swings harder. The CD version even includes “The Lady is a Tramp,” which is about as quintessential as Frank gets. It is, in a word, oke.

In a way I grew up with Sinatra. My father is a big fan and I can especially remember hearing Come Fly With Me playedcome fly with me at the house when I was a kid. The album also had a great cover, a painting of the jet-setting Sinatra preparing to board a TWA Constellation. His snap-brim hat is slightly askew and he gestures jauntily with the thumb of one hand while grasping some feminine digits that extend from off-cover with the other.

I never really fell under the spell of Sinatra myself until I attended college in Los Angeles. I remember exactly how it happened. Late one afternoon I was sitting on the roof of my apartment building, listening to KROQ on a radio and watching airplanes off in the distance descending into LAX as the evening sky turned the color of an orange popsicle against silhouetted palm trees. KROQ was a ground-breaking “new wave” rock station at the time, but this afternoon the DJ played “Come Fly With Me,” and that was it. The next day I headed off to the strip of used record stores along Fairfax Avenue and found a copy of the album. Thanks, KROQ.

At first I approached Sinatra somewhat ironically, liking the Joe Piscopo aspects of his singing, the “cats and “jacks” and “broads” and all that surface stuff. What can I say? I was a callow 21-year-old. But gradually, as I listened to the music, I discovered Sinatra as the great artist he was and always will be.

I started buying more albums, some of them the cheap reissues Capitol released in the early 1980s. The label routinely dropped songs from these new versions to save money, probably to make pressing them cheaper. A Swingin’ Affair! originally had 15 tracks, so some genius in marketing decided to leave three of them, including “Night and Day,” off the re-release. Insanity! That’s like trying to save a few pennies by leaving the meat out of the spaghetti sauce.

 It’s another grim day following a night of rain. The sky is gray and threatening but the temperatures are climbing, so it’s as warm and humid as dog’s breath. Wet leaves blow down from the trees and plaster themselves on the lawns and sidewalks. Still, I managed to get out for a walk between showers and returned home only minutes before a new deluge. Here’s what I heard on the iPod shuffle.

11 tracks (1) Walter Becker. “Hard Up Case” from 11 Tracks of Whack. A song from Becker’s first solo album, an overlooked gem. Had Donald Fagen been singing the vocals it could have been one of the best Steely Dan albums ever. Becker’s vocals aren’t bad, but they are a bit of an acquired taste. Definitely an album worth checking out. I waited a while before I bought it, and then scored it cheap in a cutout bin in D.C. I got more than my money’s worth. Becker’s follow-up, Circus Money, is also excellent.

(2) Hoodoo Gurus. “Death Ship,” from Stoneage Romeos. I got a review copy of Stoneagestoneage romeos Romeos when I was editing a now-forgotten rock magazine in Boston. That must have been back in 1983 or ’84, and I fell hard for it. It was great guitar-oriented pop, with stick-in-your-head melodies, some edginess, and a lot of humor. The band included Larry Storch (F Troop) and Arnold Ziffel (the pig from Green Acres) among the personages to whom they dedicated the album, and the title comes from a Three Stooges short. Obviously not a band that was taking themselves too seriously. I saw them on that tour when they played a place called The Channel, a big, sprawling warren of bars and side rooms in South Boston. (Either the dBs or the Replacements opened.) The Hoodoos put on a great show, even though, as I learned later, they played with borrowed instruments because theirs had been stolen from their van a night or two previously. A couple years later, after I moved to Washington, I got to interview the Hoodoos in the somewhat shabby Hotel Harrington, also home to a bar called The Pink Elephant Lounge. I was impressed when guitarist Brad Shepherd returned to the room after doing his laundry and dumped out a trash bag that seemed to contain nothing but paisley shirts.

 nightfly(3) Donald Fagen. “New Frontier,” from The Nightfly. Fagen’s solo album was the first record I ever reviewed for publication. I wrote about it for the Maine music paper Sweet Potato just after I returned East the fall after I graduated from college in California. I didn’t get paid for the review but I got the album for free, which was payment enough.

 bond(4) Garbage, “The World is Not Enough,” from The Best of Bond. I paid for half of The Best of Bond CD, splitting the cost with my son, who must have been all of seven at the time. We were both Bond aficionados. The first Bond film we all watched together as a family was You Only Live Twice, which I figured was a good place to start because it contained enough gadgets and spectacle to keep the young minds interested. It worked, especially for Sam. I still get emotional whenever I hear the great string arrangements that kick off Nancy Sinatra’s performance of the theme song. Garbage is no Nancy, but this is one of the better songs from the more recent Bond movies. The movie itself is nothing to write home about, though.

 songs in key of life(5) Stevie Wonder. “Joy Inside My Tears” from Songs in the Key of Life. It must have been 1977 when a local radio station awarded my friend Bob the opportunity to do a “record run” at the Sonnet and Song. That meant he had a minute or two to go through the record store and grab as many records as he could. In the days leading up the big event everyone in school advised Bob about what he should grab. I think all the coaching just confused him, because he didn’t snag that many albums, certainly not as many as previous record run winners had scored. He gave me a bunch—or sold them to me, I can’t remember—and I went to various department stores around town and exchanged them for albums I wanted. Anyway, I noticed that before the record run, the owners of Sonnet and Song had taken all the copies of Songs in the Key of Life and hidden them away. I guess they didn’t want Bob getting any copies of that mammoth three-records-plus-bonus-disc set for free. At some point I bought the vinyl version (when my daughter was born my wife and I used “Isn’t She Lovely” for our answering machine message), but I recently found the CD version in the library and burned it. Stevie used to be Godlike, the kind of artist who appeared on the cover of Time magazine when he released an album. He doesn’t have that stature anymore, but who does?

 stolar(6) Belly. “Feed the Tree,” from Stolar Tracks Volume 2. I first heard this song on Maryland’s WHFS back when that station was still great. I was driving down Connecticut Avenue in D.C. at the time. The song’s from Belly’s debut album, Star. I bought the CD, but I loaded this on my iPod from a great collection I ordered sometime around 1993 from Stolichnaya Vodka for some nominal charge to cover shipping. Stolar Tracks Volume 2 was a superb collection with songs from Eleventh Dream Day, Dinosaur, Jr., School of Fish, Pure, the Pooh Sticks, and a bunch of other bands who have faded into obscurity. The song by Eleventh Dream Day, “After This Time Is Gone,” turned me into a fan, even though I had already seen them live, when they opened for the Meat Puppets at a show I caught in Chicago. The Pure song, “Blast,” is also a classic.

 (7) Louis Armstrong. “S.O.L. Blues.” Shortly after getting my first CD player (a gift from my brother—I was a stubbornarmstrong CD holdout because I resented the way the record companies were shoving them down our throats with the obviously false claim that they would last “forever”) I bought a cheap Laserlight collection of early Louis Armstrong stuff, recorded with the Hot 5 and Hot 7. As a former trumpet player myself, I felt I had to have some Armstrong. Man, that cat could blow!

blow your cool (8) Hoodoo Gurus. “Good Times,” from Blow Your Cool. The Hoodoos again! This time they’re helped by members of the Bangles, who used to be great, before that “Walk Like an Egyptian” crap. I saw them once in Boston and I swear Susanna Hoffs was batting her eyes at me. I bet all the guys in the audience through that. I remember buying Blow Your Cool in DC and heading off to a friend’s house to listen to it. We played side one and then he decreed that everyone else in the room would get to play the side of an album before it was my turn again. I was pissed. It’s not the Hoodoos best, but it has a few great tracks, especially “What’s My Scene?”

 (9) Stevie Wonder. “All in Love is Fair,” from Innervisions. Stevie again! This turned out to be a great song to hear oninnervisions a gray, dreary day with the leaves falling all around. The guy had a great set of pipes.

pink panther(10) Henry Mancini. “Pink Panther Theme” from some Best of Mancini disc I got from the library. We used to play this song in my high school dance band. The sheet music had the best tempo direction I’ve ever seen: “Groovy mysterioso.” If I ever form a lounge band that’s what I’ll call it. We’ll play strange, David Lynchian cocktail jazz. I used to have the soundtrack album to The Return of the Pink Panther, still my favorite movie of the series. I remember when it came out in 1975 I was reading a Time magazine review of the movie out loud to my parents and I was laughing so hard I couldn’t get through it. And that was just a review! I think it was the description of the blind man and his “minkey” that got me. Peter Sellers was a genius. Several years ago I watched this movie with my kids and young Sam was choking with laughter when Clouseau fights with Cato. Good times. Don’t even mention the Steve Martin travesties.

sinatra brass (11) Frank Sinatra. “I Get a Kick out of You,” from Sinatra and Swingin’ Brass. I could go on for a long time about Frank. Some day I will. This is from one of his more overlooked albums, a Reprise release that was arranged and conducted by Neil Hefti. That’s another high school dance band connection—we used to play Hefti’s song “L’il Darlin’,” but at a funereal pace. It was neither groovy nor mysterioso. The Swingin’ Brass album, though, swings with a vengeance and Frank sounds great. You know it must swing hard because they had to drop the“g” from “swinging” in the title. (Why was Hefti hoarding all those gs?) Hefti, who did a lot of arranging for Count Basie, died recently. He also composed the theme song for TV’s Batman. He belongs in some Pop Culture Hall of Fame.

time passages (12) Al Stewart. “Palace of Versailles.” This song was originally from Time Passages, but I got this version from a live 1976 concert that I found on the web. There’s a skip in this song on my vinyl copy of Time Passages–I guess you could say that’s kind of a time passage itself.  Weird. Strangely enough, just before I set out on this morning’s walk WXPN played an Al Stewart song, “Sleepwalking,” from his most recent album. I had never heard it before, but it sounded pretty good. My love for Al Stewart betrays the geek side of my musical tastes. At some point today I might throw my vinyl copy of Modern Times on the turntable and give it a whirl. Maybe Past, Present and Future too.

 (13) Sinead O’Connor. “You Do Something to Me,” from Red, Hot and Blue. I’ve added a few songs to the iPod fromred hot blue this Cole Porter tribute album, which was recorded to raise money for AIDs research. Sinead does a pretty good version of this Porter tune. She’s a little breathy, perhaps, but not bad. I like to think she’s singing it to the Pope.

goodman (14) Benny Goodman Quartet. “The Blues in Your Flat” from The Legendary Small Groups. The first swing music I listened to, back in high school, was Glenn Miller. When I read books about the swing era, though, writers usually disparaged Miller and said that Benny Goodman was better, which made me resent Goodman for a while. The only Goodman we had in the house was my uncle’s LP of music from The Benny Goodman story (Steve Allen played Goodman) . It had the live Carnegie Hall version of “Sing, Sing, Sing” on it, and I played that cut over and over, mainly for the Harry James trumpet solo. (I got to see James perform a concert in Augusta, Maine, in 1977 and still have an autographed ticket stub. The concert, a “cabaret dance,” cost a whopping three bucks. At the intermission James, whom I remember as a somewhat morose old man, sat at a table in front of the stage and quietly signed autographs.)  I eventually came to realize that, yes, Goodman was better than Miller. These small group recordings are terrific.

James ticket front

My Harry James ticket.

My Harry James ticket.

 All in all, not a bad set list.  There’s nothing particularly new on it, I realize, but you can’t have everything. Because, as Steven Wright asked, where would you put it? Certainly not on an 8 gigabyte iPod.