A Guide to the Best Compilations of Frank Sinatra

The Essential Frank Sinatra: The Columbia Years-2 disc set. He's so young!

The Capitol Years, 3-disc set, 1990. An excellent intro to the best of Sinatra's Capitol work.

The Complete Reprise Studio Recordings, 1995. This is the "suitcase" box set.

The Reprise Collection, 1990. If you don't want to invest in the suitcase, get this. It's terrific.

As I mentioned in my previous post about my ten favorite Frank Sinatra albums, Frank Sinatra recorded a ton of material over his long career, some 1,100 songs in all. And that’s not counting songs he recorded for radio or television that he never officially put on records. Sinatra was also prone to re-record songs he liked throughout his career, which gives us some fascinating insights into how his approach to singing changed over the years, but it also might make his discography slightly confusing for newcomers. So where do you start with Sinatra? It’s a tough question, and considering there are about a million different Frank Sinatra compilations out there, it makes for many possible entries into the Sinatra discography. This post is a guide to what I think are the best compilations of Sinatra’s work.

To give just one example from Sinatra’s discography of how he re-recorded songs again and again, let’s take a look at the number of times he recorded the Cole Porter classic “Night and Day.” (Will Friedwald goes through all the different versions of “Night and Day” in his excellent book “Sinatra! The Song Is You.” He also includes live versions, so his list is a lot longer than this.) The version of “Night and Day” most listeners are familiar with is probably the swinging version Sinatra recorded of Nelson Riddle’s arrangement on his 1957 album “A Swingin’ Affair!” But Sinatra had first recorded the song in 1942 for the Bluebird label, a subsidiary of RCA, while he was with Tommy Dorsey’s big band. Sinatra also recorded the song for Columbia in 1947, but this version would remain unreleased until 1993. Sinatra’s next recording of “Night and Day” was the famous up-tempo version with Nelson Riddle, recorded for Capitol in November 1956. Sinatra then recorded a ballad version in 1961 for his Reprise Records label, arranged by Don Costa. This version was released on the excellent “Sinatra & Strings” album. Sinatra’s final recording of “Night and Day” was a disco version from 1977. Nope, I’m not kidding. It’s terrible, in case you were wondering. So that leaves us with 5 different studio recordings of “Night and Day,” all from very different periods of Sinatra’s career. So how do you know which version of “Night and Day” you’re getting? You need to check the record label of the compilation. I can guarantee you’ll never get the disco version, as I don’t think that’s been on any compilations except the 20-disc set of his complete Reprise recordings. 

So let’s start examining Sinatra’s compilations, in chronological order. I’m really not familiar enough with Sinatra’s work with Tommy Dorsey from 1940-42 to comment very much on it. I don’t own the box set “The Song Is You,” which collects all of Sinatra’s work with Dorsey on 5 discs. If you’re interested in this period, pick up a single-disc compilation and if you absolutely love it, just get the box set.

The Columbia Years-1943-1952:

Unless you’re a Sinatraphile like me, you probably don’t need the 12-disc set of all 285 of Sinatra’s Columbia Recordings. But it’s out there if you want it, and it’s the only way to hear the majority of Sinatra’s work for the label.

“Frank Sinatra Sings His Greatest Hits”-1 disc-1997: This is an excellent single-disc overview of Sinatra’s best-known Columbia songs, and would be a good place to start if you’re not familiar with this era of his career.

“Portrait of Sinatra: Columbia Classics”-2 discs-1997: This collection, which was reissued as the 2-disc “The Essential Frank Sinatra: The Columbia Years” in 2010, offers a good, slightly more expansive overview of his Columbia songs. This would also be a good starting point for the Columbia years. Curiously, it’s missing “Oh, What It Seemed to Be,” one of Frank’s biggest hit singles of the period.

“The Essential Frank Sinatra: The Columbia Years”-1 disc-2003: To confuse matters, in 2003 Columbia issued a single-disc “Essential Frank Sinatra,” which is very different from the “Portrait of Sinatra/Essential Sinatra” 2-disc set. This single disc covers much the same ground as 1997’s “Frank Sinatra Sings His Greatest Hits,” but 8 of the songs are presented in previously released alternate takes. While the alternate takes aren’t that different from the originals, it’s odd that they put so many on a bargain budget compilation. Stick with the other Columbia comps.

“The Best of the Columbia Years: 1943-1952”-4 discs-1995: While it may seem a bit hefty to those just starting to explore Sinatra’s Columbia years, this box set collects just about all of Sinatra’s absolutely essential Columbia songs. Highly recommended if you don’t want to splurge for the 12-CD Complete Recordings. Contains great songs like “Close to You,” and “I Fall in Love Too Easily” that the other sets don’t have.

The Capitol Years-1953-1962:

“Frank Sinatra Sings the Select Cole Porter”-1 disc-1965: For a single-disc overview of Sinatra’s Capitol years, you could do a lot worse than this excellent disc that collects songs by Cole Porter, which also happen to be some of Sinatra’s greatest songs of the period. Expanded to 16 tracks on CD in 1991, this album features “I’ve Got You Under My Skin,” “Night and Day,” “I Get a Kick Out of You,” “Anything Goes,” and “Just One of Those Things.” Highly recommended for the neophyte.

“The Capitol Years”-3 discs-1990: An interesting thing about Sinatra’s Capitol output is that he deliberately kept single and album releases very separate, which means that you could own every single concept album Sinatra made for Capitol, but you would still be missing such key tracks as “I’ve Got the World on a String,” “Young at Heart,” “Three Coins in the Fountain,” “Learnin’ the Blues,” “Love and Marriage,” “(Love Is) The Tender Trap,” “All the Way,” and “Witchcraft.” That’s because those songs were only issued as singles. Capitol collected those singles as hodge-podge albums at the time, like “This is Sinatra.” But if you want the hit singles along with the classic album tracks, you need to get a set like “The Capitol Years,” which collects the best of the Capitol singles and albums. There are a few rarities sprinkled throughout the set, like an amazing version of “One for My Baby” with just Sinatra and Bill Miller’s piano backing him, and the previously unreleased “Here Goes.” I would highly recommend this set; it’s the best introduction to Sinatra’s Capitol work. From here you can figure out which albums you absolutely need to own. (Spoiler alert: It’s all of them!)

“The Complete Capitol Singles Collection”-4 discs-1996: Once you have all of Sinatra’s Capitol albums, you’ll need this box set to get all of his singles in one place. I wouldn’t recommend this for a starting point for Sinatra’s Capitol work, as his singles were much more uneven in quality than his albums. And since this set doesn’t include any of Sinatra’s album songs, it doesn’t really function as a best-of. 

“Concepts”-16 discs-1992: Yes, you read that right. The massive “Concepts” box set collects all of the concept albums that Frank Sinatra recorded for Capitol. Which means you get such classics as “In the Wee Small Hours,” “Songs for Swingin’ Lovers!” “A Swingin’ Affair!” “Come Fly with Me,” “Come Dance with Me,” and “Only the Lonely,” all in one place. You’ll eventually need all of these albums, because they’re all amazing. “Concepts” also includes “Frank Sinatra Conducts Tone Poems of Color,” which features Frank behind the podium, not behind the microphone. 

“Sinatra 80^th: All the Best”-2 discs-1995: I don’t own this set, but it has a really weird track selection. It’s 40 songs on 2 discs, and one of the tracks they pick is “Wait for Me (Theme from Johnny Concho)”. Really? That’s one of Sinatra’s 40 best Capitol songs? Nope, you’re wrong. It also features a spliced-together duet of Sinatra and Nat King Cole on “The Christmas Song.” Not recommended.

“Classic Sinatra: His Greatest Performances 1953-1960” and “Classic Sinatra II.” These single-disc comps from 2000 and 2009 have a much better track selection than “Sinatra 80^th”. Both “Classic Sinatras” are a mixture of hit singles and great album tracks which are a superb introduction to Sinatra’s Capitol years. It doesn’t include the hit single “Hey! Jealous Lover,” but you’ll survive without it. If you don’t want to spring for “The Capitol Years,” pick up these 2 instead.

The Reprise Years-1960-1988:

“A Man and His Music”-2 discs-1965-66: This was the Grammy winner for Album of the Year in 1966, giving Sinatra back-to-back wins in the category, as “September of My Years” had won in 1965. Issued in conjunction with an NBC TV special of the same name, to commemorate Sinatra’s 50^th birthday, “A Man and His Music” is a rather silly listen now, as Sinatra narrates highlights from his career. The songs are first-rate, of course, but they’re not the original hit recordings from Columbia or Capitol, but rather re-recordings Sinatra had made for various Reprise projects in the early 1960’s. To show how many songs he had re-recorded, just 3 songs were specially re-recorded for this project. This isn’t a good introduction to Sinatra’s Reprise years, and his narration often intrudes on the beginning of songs.

“The Reprise Collection”-4 discs-1990: Issued to celebrate Sinatra’s 75^th birthday, this is an excellent introduction to Sinatra’s work on Reprise. Features all of his most famous songs from the 60’s and 70’s, as well as many key album tracks and some rarities that were previously unreleased. Highlights include: “Come Rain or Come Shine,” “I Have Dreamed,” “Luck Be a Lady,” “The Way You Look Tonight,” “My Kind of Town,” “Fly Me to the Moon,” “It Was a Very Good Year,” “Strangers in the Night,” “Summer Wind,” “That’s Life,” “Once I Loved,” “Drinking Again,” “All I Need is the Girl,” “My Way,” “Theme from New York, New York,” “The Gal that Got Away/It Never Entered My Mind.” Highly recommended.

“Sinatra Reprise: The Very Good Years”-1 disc-1991: A single-disc of highlights from “The Reprise Collection,” this is an excellent single-disc intro to Sinatra’s biggest hits on Reprise, but it inevitably lacks the depth that “The Reprise Collection” offers. This was one of the first Sinatra CD’s I owned, and one of my first introductions to his music, so I do have a soft spot for it.

“Everything Happens to Me”-1 disc-1996: This is a very interesting compilation, as it’s not meant to be a “Greatest Hits” package, but a collection of deep cuts from his catalogue. Sinatra chose the tracks himself, and while it is a somewhat downbeat listen, there are many standout Sinatra tracks here. Highlights include: “The Gal that Got Away/It Never Entered My Mind,” “Summer Wind,” “Once I Loved,” “The Second Time Around,” “Come Rain or Come Shine,” “Drinking Again,” “How Insensitive,” and “Put Your Dreams Away.” Recommended for the curious, but you won’t find “My Way” here.

“The Very Best of Frank Sinatra”-2 discs-1997: This has a good track selection, but be sure you know you’re getting the Reprise re-recordings of his Capitol hits, not the originals. The track list is very heavily weighted towards famous Capitol songs.

“My Way: The Best of Frank Sinatra”-2 discs-1997: Whoever put this together has a funny idea of Sinatra’s “best.” Sinatra’s versions of “Bad, Bad Leroy Brown” and “Mrs. Robinson,” both of which are included here, are among his worst recordings ever. Why someone would put those on a compilation, I have no idea. This set gets bonus points for including “The Girl from Ipanema” with Antonio Carlos Jobim. Minus points for including “America the Beautiful” from the “Concert Sinatra” sessions rather than “I Have Dreamed.” Not recommended. 

“Romance”-2 discs-2004: This is an interesting collection, based around a theme rather than just his greatest hits. The track selection is really quite good. It includes several songs with Antonio Carlos Jobim, and the excellent “I Have Dreamed.” This would be an excellent purchase and introduction to Sinatra’s work in the 60’s and 70’s. Just know that it doesn’t include “My Way,” “My Kind of Town,” and “Theme from New York, New York” on it.

“Sinatra: Best of the Best”-1 disc-2011: This is the only album that has both Capitol and Reprise recordings together on the same disc! Yay for cross-licensing! For an artist of Sinatra’s stature, you’d think that his various labels would get together and issue a 4 or 5 disc set of his absolute best recordings for Columbia, Capitol, and Reprise. It’s odd that’s never happened. Of course, his catalogue is deep enough you can do a 4 disc set for each label and just scratch the surface of what he did. For a 23-track compilation, “Best of the Best” is actually a pretty good selection. Although I do have to quibble with the choice of “Love and Marriage,” which is not among my top 23 Sinatra songs. It could have easily been replaced by “I Get a Kick Out of You,” to name just one better song. But there’s no way this disc could be perfect. I actually own the 2-disc version of “Best of the Best,” because that included the long out-of-print 1957 Seattle concert with Nelson Riddle, which is recommend for Sinatraphiles. 

“The Complete Reprise Studio Recordings”-20 discs-1995: Yep, you read that right, 20 discs! 452 songs! Originally issued in a limited edition of 20,000 to celebrate Sinatra’s 80^th birthday, the set was shaped like a suitcase, complete with handle on top. In 1997 I bought the suitcase limited edition from Collector’s Choice Music, as they had the last 20 or 30 copies available. I was 16 years old then and spent most of my summer earnings on this massive set, which set me back a little more than $400 bucks. Of course, in the fall of 1998, Reprise issued the set at a much lower-price, in an unlimited edition, which cost about $250. Oh well, my set looks cooler. While this set might sound like overkill, there are many great Sinatra songs during his Reprise years that fell through the cracks but are collected on this set. Unfortunately, Reprise was never as good at issuing CD’s as Capitol was, so it’s also very hard to find all of Sinatra’s Reprise albums on CD. Recommended for the advanced Sinatraphile, but keep in mind you’ll still have to get the live albums “Sinatra at the Sands” and “The Main Event” to completely cover this part of Sinatra’s career.