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Frank Sinatra: The Essential Albums, Movies, and Books

The essential music, movies, and books to start your Sinatra collection

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No pop singer was arguably as famous as Frank Sinatra at his zenith, but then again, with the possible exception of John Lennon, none were so hard to personally fathom, a thicket of contradictions that formed the turmoil which fueled his greatest achievements. While ten items aren't enough to fully explain Ol' Blue Eyes, they go a long way towards beginning the journey. Here are the essential albums, books, and movies that are the components of any basic Frank Sinatra collection.

1. The Essential Frank Sinatra: The Columbia Years

Before he was the greatest pop singer of all time, Frank Sinatra was merely the biggest teen idol of all time; not much of a crooner compared to what he would become, but who is? This essential two disc, 36-track retrospective gives you all the hits and just enough of the deep cuts to paint a portrait of The Voice as a young man, focusing on Sinatra as interpreter as first and hitmaker second and therefore leaving out fluff like "The Hucklebuck" and "Mama Will Bark." (Not to be confused with an earlier single disc collection with the same name and a different cover!)
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2. In the Wee Small Hours

Before the Beatles or even Ray Charles got to it, Sinatra created the concept album. Realizing his new adult audience bought albums more than singles, he concentrated on keeping one mood constant throughout an album. In the Wee Small Hours, a series of haunting post-breakup ballads of regret and remembrance, may be his single greatest work. Recorded not long before his final tortured break from his second wife Ava Gardner, it's certainly his most personal. So much so that he himself broke down during the late-night sessions.
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3. Songs for Swingin' Lovers!

Then again, Frankie was never one to stay in place, artistically or otherwise, and thus his follow-up album was a literal uptempo affair designed to celebrate the joys of new love. The swinging Sinatra is in full effect here: "You Make Me Feel So Young," "I've Got You Under My Skin," "You're Getting to Be a Habit With Me." A companion piece of sorts to Hours, right down to the album art.
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4. Frank Sinatra MGM Movie Legends Collection

Even more so than Elvis, Frank was considered a potential master thespian whose own worst enemy was his lackluster work ethic when it came to anything but singing. Unlike Elvis, Sinatra managed to deliver a few classic performances to prove it. This DVD collection features five movies showcasing the triumphs (the original Manchurian Candidate) trifles (the fun romp of Guys and Dolls) and the trainwrecks (Sinatra as a Spanish guerrilla fighter with a notoriously labored accent in The Pride and the Passion).

5. The Capitol Years

Artistically, the Voice finally came into his (its) own after the early '50s career renaissance set off by his stunning turn in From Here to Eternity. Singing for lovelorn adult males now instead of starstruck pubescent girls, Sinatra transformed the "saloon singer" into high art, and although some of the tracks on this generous 3-disc set repeat on Wee Small Hours and Swingin' Lovers, his artistry is well worth that redundancy. With 20 albums in just eight years, any single-disc retrospective is laughably incomplete.
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6. Frank Sinatra: Vegas

To this day, there still isn't enough live Sinatra of quality out there, but this 2006 box set does the most heavy lifting when it comes to the town he helped build. His early '60s reign at the Sands casino is documented in this collection by two separate and full night shows, but there's also two very different portraits of a ragged but regal '80s Frank, and a long-bootlegged DVD capture of an infamous 1978 Caesar's Palace gig. His between-song rants are edited out, but really, that's for the best.
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7. Sinatra Reprise: The Very Good Years

Now a certified walking talking showbiz landmark, Ol' Blue Eyes engineered a series of amazing comebacks, looked back with classics like "That's Life" and "It Was a Very Good Year," and enjoyed more and bigger hits than ever: not just "Strangers in the Night," which stormed the hippie pop scene in 1966, but also "Night and Day," "Love and Marriage," and his career capper, "New York, New York." The first album for Sinatra neophytes to hear.
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8. "His Way: The Unauthorized Biography of Frank Sinatra," Kitty Kelley

Yes, it's a hatchet job. It's the original celebrity hatchet job, bringing the ugliest stories of Frank's career out from the tabloids and gossip columns into the mainstream spotlight, and while he was still alive, to boot. But it's also verified, direct remembrances from those he'd wronged, and it's invaluable in understanding Sinatra's dual nature. Even if this potboiler only gives the one side, it's a side that needs to be taken into consideration.
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9. Rat Pack: The True Stories of the Original Kings of Cool

The definitive story of Frank's famous celebrity entourage, begun as Humphrey Bogart's drinking club and later put on full view in the original Ocean's 11 film, has yet to be told. But this 3 1/2 hour (!) A&E documentary, complete with interviews from equally famous Pack satellites, does a fine job anyway. It explains not just the formation of the group that ruled Vegas in the swinging '60s, but also their dynamics, both on and off stage and in the movies. Joey Bishop fans probably won't get much out of it, but who went to the show to see Joey?
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10. Frank: The Voice

This, on the other hand, is the most balanced of the Sinatra biographies, avoiding both the mudslinging and outright hagiography that his biographers seem to always veer between. Instead, author James Kaplan delves deep into the mostly unexplored recesses of the Chairman of the Board's childhood in an effort to explain his seemingly irreconcilable contradictions, then uses those insights, like a novelist would, to develop a plausible scenario explaining the inner workings of Frank's soul. Happily, it also includes a thorough exploration of Sinatra's landmark interpretive approach to his vocals.
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