If You're Only Going to Buy One Greatest Hits Set From... Frank Sinatra

In 1979, as a senior in high school, I doubt I could have pictured myself ever buying a Frank Sinatra album.  By 1983, I had purchased my first Sinatra (the underrated 1981 saloon album She Shot Me Down, then a remainder on vinyl and now hard to find on CD but available for download, and I recommend it highly).  I added a few albums here and there over the years, occasionally going on small binges.  Right now, I find myself with 34 Sinatra albums (27 on compact disc, five on vinyl, two more on cassette), and I’m still trying to expand the collection.  Almost every song he does is interesting to me – even the misguided attempts to adapt his style to rock, or a 1977 attempt to appeal to the kids by giving “All or Nothing at All” and “Night and Day” disco arrangements.

I should point out that Sinatra hardly did all of this alone – he wasn’t a songwriter, and he didn’t play an instrument.  But he studied and worked hard to improve and hone his voice, and surrounded himself with some of the best arrangers ever – Billy May, Nelson Riddle, Gordon Jenkins, and Don Costa come to mind as his best.  He also had great taste in material for the most part, and after a while Tin Pan Alley songwriters wrote songs specifically for him.  Finally, he recorded everything live in the studio with a full orchestra, not multitracking.  (The exceptions were the 1990s Duets albums, where his duet partners recorded their parts separately – which wound up being the main point critics homed in on.)

As you can imagine, having recorded hundreds, perhaps thousands of songs, there are a bunch of compilations out there.  He also recorded with Harry James and Tommy Dorsey in the 1930s and 1940s before going solo.  The James sides are on various small labels, but the Dorsey albums were on RCA (now part of Sony), and Sinatra recorded solo for Columbia (also part of Sony), then Capitol (now part of Universal Music Group), before starting his own label, Reprise (which was bought out by Warner Brothers in 1963).  His final two Duets albums returned him to Capitol.

Since Sinatra’s death in 1998, all three labels have been releasing the occasional anthology, usually shuffling around his better songs with the occasional oddity, and almost always including an alternate version, unreleased track, or remixed song to lure in collectors.  The result, of course, is trying to find an all-encompassing set is a challenge, since record labels don’t always play nice with one another.  I have six different compilations (including one that I didn’t realize was a compilation until recently; I thought it was another studio album) – two each on Capitol, Columbia, and Warner Brothers, and there are no songs leased from other labels.  But, happily they’ve cooperated enough so there is one choice to get that covers virtually his whole career.

Ultimate Sinatra: The Centennial Collection

This is the one set that covers his career with all three labels (it’s possible there are a couple of Dorsey songs sprinkled in there but I’m not entirely sure; the leadoff version of “All or Nothing at All” is with Harry James).  A little over half of the first disc represents the Columbia years (which, in my opinion, is all you need – the arrangements and sound of the day is nothing like the Sinatra we came to know), while the last disc and a half is all from the Reprise years, with the rest from Capitol.  Some choices I’d quibble with (I could easily live without “All Our Tomorrows,” and “Something Stupid” lives up to its title), but some songs that I could listen to forever (including the Trilogy version of “It Had to Be You,” which we used as our first dance song at our wedding after hearing it in When Harry Met Sally).  At $26.44 for four discs, it’s a bargain.  There’s got to be a way to download it off Amazon, but they’re not making it easy to determine – and since the physical edition has an 80-page book, that’s probably the way to go anyway.  (It’s $39.99 on iTunes, which is less of a bargain.)  Important note:  there’s also a single CD version (that does not include “The Centennial Collection” in the title) available for an $11.99 download on iTunes; it’s perfectly okay (and would be among the best of the single-disk options), but it doesn’t have the breadth of the four-disc set.

Let’s look at the others label by label.  Links go to Wikipedia, and I’m skipping some of the lesser sets that are out of print.  Still, this is easily the longest list I’ve ever accumulated for these pieces, which gives you an idea of the choices.

RCA/Columbia:  These were two separate labels in the good ol’ days, but now are one (Sony owns them both), so the Tommy Dorsey and early solo years can be found here, along with some of the Harry James sides.  This is good for nostalgia purposes, but honestly, I’ve never said to myself, “I need more of the Columbia years!”

The Columbia Years 1943-1952: The Complete Recordings (1993) – all 285 songs he recorded for Columbia during that era (the Harry James and Tommy Dorsey sides aren’t here, however) on 12 discs.  Again, this is a lot of less-than-prime Sinatra to wade through, I suspect.  Out of print, but available for download for $99.99.  It also appears Columbia hacked this up into 12 individual CDs as well.  I have access to free downloads of Sony music through my public library (five songs per week), so I may take a year or so to download this.

Portrait of Sinatra: Columbia Classics (1997) – this is the one I have, and it may be all you ever need.  36 songs, avoiding the goofier stuff A&R label man Mitch Miller urged him to record late in his tenure there (“Mama Will Bark,” “The Hucklebuck”).  It’s kind of like listening to the first few Beatles albums – they’re okay, but sooner or later you’re going to want to hear Revolver or Abbey Road.  Only one copy left at Amazon for $15.99, but they’ve rereleased it under the Essentials banner as The Essential Frank Sinatra: The Columbia Years (good for Sony acknowledging you won’t find everything here) at $9.99.  It’s not available for download through Amazon, however; iTunes has it at $14.99.

The Best of the Columbia Years: 1943-1952 (1998) – a four-CD box set that arrived very late in the game (Capitol and Reprise had released similar, and completing, box sets in 1990); Columbia did release the four-CD The Voice (now out of print) in 1990, but it was resolutely ignored in the stampede to get the Capitol and Reprise boxes.  Again, it stays away from the sillier stuff, but I’m not sure if more is necessarily better here.  Out of print; it seems to be available used on Amazon cheaply.

The Essential Frank Sinatra with The Tommy Dorsey Orchestra (2005) – issued by Sony in 2005 after they acquired the RCA catalogue.  I’m sure this isn’t everything they released, but it’s a lot of music – and remember, there weren’t very many albums issued in the late 1930s.  $13.99 for the CD, $7.12 for the download, so that’s probably the way to go.

Capitol:  It’s almost impossible to go wrong with any of prime Capitol material, so I’ll try to point you to the best bang for your buck.  Sinatra recorded for Capitol from 1953 to 1962 (he also made the two Duets albums, released in 1993 and 1994, for the label, but wisely they haven’t been included in any compilations to my knowledge).  Capitol let his catalog slip into disrepair in the 1960s and 1970s (including issuing cheap two-album sets with ugly, more modern covers), but they pulled their act back together in the late 1980s.  Many of his original studio albums have been rereleased with bonus tracks, but you might want to dip a toe in the water before going that route.

This Is Sinatra (1956), This Is Sinatra Vol. 2 (1958), Look to Your Heart (1959) and All the Way (1960) were made up of singles and B-sides from the era, music that wasn’t included on studio albums – at that time, Capitol and Sinatra were releasing singles separately from the albums, so fans would have to make two purchases.  (The singles were perhaps a touch more commercial as a result.)  This Is Sinatra contains “Learnin’ the Blues,” the only #1 single Sinatra had at Capitol.  All are out of print on CD and unavailable for download, but Capitol has reissued the original versions of all but All the Way on vinyl, if you’re a collector.  They’re perfectly listenable – for years I thought my copy of All the Way was a regular studio album.

The Capitol Collectors Series (1989) – a 20-song shuffle (this would become common, even though they could probably fit 30 songs on a single CD), with few rarities (except perhaps “I’m Walking Behind You”).  Out of print and unavailable for download, but easily found in used CD shops.

The Capitol Years (1990) – okay, start here.  A three-CD box that includes both singles and prime album cuts.  Virtually nothing rare, but definitely the cream of the crop, and the box that got me started on Sinatra for good.  I bought this then because it was cheaper than Reprise’s box by half (I want to say it was about $30 for three discs, as opposed to roughly $60 for four Reprise discs), but it’s even cheaper today ($22.57 new on Amazon, not available for download).  I just saw two copies for $7.99 each used at Half-Price Books (seriously, who’s getting rid of these?), so you have options.  It’s an absolute necessity to hear him during his peak years, and song for song is probably better than Ultimate Sinatra; it just lacks that set’s scope.

The Best of The Capitol Years (1992) – exactly what it sounds like:  20 songs taken from the three-CD box The Capitol Years.  I strongly recommend getting the original.  $26.95 for the CD on Amazon and no download, which indicates to me Capitol is clearing out inventory.  You can probably find it at a used CD store cheap if you insist.

Concepts (1992) – all of the studio albums are here, along with the somewhat-hard-to-find Frank Sinatra Conducts Tone Poems of Color, but none of the singles, and nothing from soundtracks.  At $199.99 for the download on either Amazon or iTunes (it’s out of print physically), it makes much more sense to get the albums individually.

Sinatra’s 80^th: All the Best (1995) – released along with Sinatra’s 80^th: Live in Concert to celebrate his 80^th birthday by Capitol.  It’s only Capitol songs, with a mashup duet with the long-dead Nat King Cole on “The Christmas Song” to lure in collectors.  Not bad, but I can’t imagine picking this over The Capitol Years.  Out of print, but available for download from Amazon ($18.99) and iTunes ($19.99), so that is an advantage over The Capitol Years for anyone who wants something heftier than a single disc.  

The Complete Capitol Singles Collection (1996) – I don’t have this, and I really must add it to the shopping list.  As noted before, Sinatra usually released singles altogether separately from albums during his Capitol tenure, so those best-of albums only on vinyl and this would be the best places to get these songs – and there’s nothing wrong with these sides, which include “Young at Heart,” “Someone to Watch Over Me,” “Love and Marriage,” “Chicago,” “All the Way,” and lots of other prime songs.  $39.99 for the download on iTunes and $42.49 for the same on Amazon.  The 4-disc set is $49.99 on Amazon, but it comes with a fairly extensive booklet, including an essay by Will Freidwald, who’s as good at analyzing Sinatra’s music as anyone.

The Capitol Years (1998) – unfortunately, Capitol used the same title for a 21-disc set of everything Sinatra released for Capitol (excluding Tone Poems of Color and a Christmas album), after Reprise had success with a similar box set.  Most of Capitol’s box sets were all-encompassing (Concepts and The Complete Capitol Singles Collection would accomplish the same thing), so this went out of print pretty quickly.  It now fetches from $250 and up as a used item.

Classic Sinatra (2000) – well-chosen 20-song compilation; all of the usual popular songs are here, along with a couple that didn’t make the Capitol box (“My Funny Valentine,” “Oh! Look at Me Now”).  It could be longer – it clocks in at just under 60 minutes, so another five songs or so could have been added to fill the limits of a single CD.  $7.93 for the disc and $11.49 for the download on Amazon.  Capitol released a Classic Sinatra II follow-up in 2009, which seems to have gone out of print quickly, and isn’t available for download (an unreleased “This Can’t Be Love” is the lure track).

Classic Duets (2002) – fortunately, not selected from the 1990s Duets albums, where Sinatra’s voice was past its peak; unfortunately, it’s not really a best-of.  These are all from Sinatra’s flop 1957 ABC television series (he thought he could do a few variety shows himself and a few dramas with other people starring and his name attached).  So they’re all recorded live, and some are better than others, but it’s different, at least.  Out of print.

Romance: Songs from the Heart (2008) – about 90 percent of Sinatra’s songs concern affairs of the heart, so this isn’t that different than anything else around.  21 songs, but only 50 minutes long, with an alternate version of “Nice ‘n’ Easy” being the new track.  Out of print on disc, but a surprising $6.99 for the download on iTunes, which usually charges more than Amazon.

Sinatra at the Movies (2008) – another not-really-a-best of; these are all move soundtrack songs.  A few rarities here, and some songs left out (nothing from Guys and Dolls?), but this is more of a curio than anything else.  Not available for download, and it looks to be out of print based on Amazon having one copy available through a secondary seller.

Sinatra: Best of the Best (2012) – one of the first albums mixing Capitol and Reprise material.  Available with and without a 1957 concert, just to confuse people.  Skip it.  $48.98 for the single-disc version on Amazon, which I don’t understand at all.

Reprise:  Sinatra was recording like crazy in the 1960s, with albums from his own label Reprise and Capitol overlapping one another (he later sold Reprise to Warner Brothers Records and continued to record for them – at one point Reprise had several other artists under their umbrella, but for most years it was just Sinatra and the similarly challenging Neil Young).  Between 1961 and 1966, he released 25 studio, Christmas, and live albums under his name – and at some point, someone might have whispered in his ear, “You know, sometimes less is more.”  After his early 1970s temporary retirement, he cut back on recording significantly, and that seemed to improve the quality, even as his voice frayed a bit.

Sinatra ’65 (1965) – standard-issue selection of singles and B-sides.  Sinatra was pushing so much product on the marketplace, this didn’t even clock in at 30 minutes, and I’m sure he had other albums of that length or less.  “My Kind of Town” and “Luck Be a Lady” are here, but you can find them almost anywhere.  $6.99 for the download on Amazon or iTunes, $12.82 for the CD, $22.99 for the vinyl copy.

A Man and His Music (1965) – released for his 50^th birthday and a television special.  I’ve heard good things about this, but although it encompasses songs from his entire career, the recordings are only Reprise versions – he rerecorded a bunch of music in those first few years.  (I should point out that I’m not necessarily against rerecordings in Sinatra’s case – his 1966 version of “All or Nothing at All” from the Strangers in the Night leaves his 1940s hit version in the dust – but be aware what you're getting.)  $14.49 for the Amazon download and $14.99 on iTunes; $19.67 for the two-disc physical album on Amazon – and I really have to grab a copy of this sometime.  A follow-up Part II album is long out of print.

Greatest Hits (1968) – well, if you want “Strangers in the Night,” “That’s Life,” and “Somethin’ Stupid” all in one place, here they are.  (This also contains “It Was a Very Good Year” and “Summer Wind” as well, so there are some true classics here too.)  Again, these songs are on much better anthologies (although there are a few songs here that are hard to find, such as “Forget Domani”).  Now out of print and unavailable for download.

Greatest Hits, Vol. 2 (1972) – released during his “retirement,” this includes “My Way” and a few choice songs from Cycles and A Man Alone.  Of course, if you really want to hear him remaking Little Anthony & The Imperials “Goin’ Out of My Head,” that’s here too.  Amazon has some CDs gathering dust (they’re going for nearly thirty dollars), and even a few cassettes, but no download availability.

The Reprise Collection (1990) – released around the same time as The Capitol Years, and a worthwhile companion.  There are more peaks and valleys than the Capitol set, but also more unreleased tracks, and a few surprises (who knew that the B-side of “Goin’ Out of My Head” was the undiscovered gem “Forget to Remember”?).  There’s a one-disc distillation of this called The Very Good Years that Amazon is clearing out (again, it’s over thirty dollars), and it’s unavailable for download, but a good used CD store should have this someplace.

The Complete Reprise Studio Recordings (1995) – this is somewhat of a holy grail for Sinatra fans in its original version, which came in a suitcase (oh, for 1990s box set packaging).  Every note he recorded for Reprise is here, including some stuff that was barely released (a second Sinatra-Jobim album, a false start on an album where all the songs were women’s names, the 1977 disco misfires that were called back after his musician friends rightly convinced him they were pretty bad).  The standard cardboard box set is out of print but starts at about $135 on Amazon; the suitcase starts at around $450, in case you have an unexpected windfall.  Not available for download.  There’s also a Reprise Years Collection from 2010 that’s also out of print; it has all the Reprise albums as individual discs but skips the greatest hits sets and singles, so Complete Reprise Studio Recordings should be preferred.

The Very Best of Frank Sinatra (1997) – well, his best on Reprise, anyway.  Two-disc set, well chosen, nothing too annoying (such as his version of “Mrs. Robinson” that I imagine makes most listeners grit their teeth).  Out of print, and unavailable for download.  I got this for a dollar used at our library, and it’s useful as a shorter option to The Reprise Collection. UPDATE: Note the songs he made famous during the Capitol years (“Love and Marriage,” “Witchcraft”) aren’t the versions that show up here; they’re rerecordings he did during his first few years on Reprise.

My Way: The Best of Frank Sinatra (2000) – I guess somebody else at Reprise decided he or she could do a better job of choosing a two-disc Sinatra than the one who picked The Very Best of Sinatra.  Also out of print; it does have 46 songs as opposed to Very Best’s 40, but they’re about the same running time.

Greatest Love Songs (2002) – somebody at Warner Brothers needs a good kick in the rear:  allowing this to stay in print but deleting The Reprise Collection boggles the mind.  The usual love songs only format, and remember some of these are Reprise rerecordings of Capitol hit versions.  $14.96 on disc.

Nothing But the Best (2008) – I’m stunned that this one-disc set is the only Reprise anthology available easily in print and for download; I’m sure somebody has an explanation for this somewhere.  The usual shuffle of popular songs, with a couple of rarities (a previously unreleased version of “Body and Soul”), and apparently there are options for a 1960s-era Christmas album and a DVD concert in the physical package, although these may no longer be available.  $11.49 to download on Amazon, $11.99 on iTunes, $14.99 for the one disc on Amazon.

Before buying anything, I have a couple of recommendations.  First, listen some of his music on streaming audio, to get the idea of what you like (don’t just look for “My Way,” “Strangers in the Night,” and “Theme From New York, New York”).  I’m not much of a Spotify person, but TuneIn radio has plenty of Sinatra-only options.  Sid Mark and Jonathan Schwartz have spent years doing Sinatra radio shows weekly in New York, and they’re a good place to start in – and given Mark is 83 and Schwartz is 78, now is the time to check them out.  I preferred Mark over the years (his show was on Saturday nights, which seemed a more appropriate time), but that’s personal preference.  Second, get a copy of Sinatra: The Song Is You by Will Freidwald out of the library.  Unlike most Sinatra books which are either family-written narratives or penned by gossipmongers looking for an argument, this focuses only on his recordings, and while he’s blunt (and I don’t always agree with his opinions), he’s honest and knows his subject.