My Top Ten Favorite Frank Sinatra Albums

Frank Sinatra in the recording studio, 1950's.

Over more than 50 years as a recording artist, Frank Sinatra recorded more than 1,100 songs that were commercially released during his lifetime. It’s a staggering amount of material. So where do you start with Sinatra? Personally, I prefer his Capitol and Reprise recordings over his early work with Tommy Dorsey and his 1940’s ballads on Columbia. I think that pretty much everything Sinatra recorded from 1953 until 1969 is amazing and wonderful. But if you’d rather not buy all 44 of the albums he made during those years, I bring you a condensed list, my desert island Top Ten favorite Frank Sinatra albums, in no order. The only rule I made for myself is that I couldn’t include any greatest hits compilations.

In the Wee Small Hours-1955-A classic of love lost, 16 tracks of pure sadness and heartbreak. Achingly beautiful, Nelson Riddle’s arrangements are the perfect complement to Sinatra’s voice.

Songs for Swingin’ Lovers!-1956-One of his very best swing albums, this features “I’ve Got You Under My Skin,” widely considered to be the single greatest Sinatra recording. Again, the arrangements are by Nelson Riddle.

Close To You-1957-When I first became a Sinatra fan in the mid 1990’s, this was the great white whale of Sinatra’s Capitol albums, as it had gone out of print. All of his other Capitol albums were in print and readily available, but this one was nowhere to be found. I scoured record stores constantly, but with the Internet still at a primitive stage, I never found it. When it was finally reissued in 2002, I quickly scooped it up. It’s an unusual album, as it features Sinatra backed only by the Hollywood String Quartet. But it’s an album of astonishing beauty, perfectly arranged by Nelson Riddle. Check the bonus tracks for the humorous song “There’s a Flaw in My Flue,” which Sinatra apparently included on test pressings of the album to see if Capitol executives were paying attention. Trivial note: the album cover is one of the few Capitol albums where Sinatra is not wearing a hat or smoking a cigarette.

A Swingin’ Affair!-1957-Similar in sound to “Swingin’ Lovers,” this is another swing album with Nelson Riddle. It features many of Sinatra’s best recordings, from the album opener “Night and Day,” “I Won’t Dance,” “I Wish I Were in Love Again,” and “At Long Last Love.” Features four songs by Cole Porter, one of Sinatra’s favorite songwriters. 

Frank Sinatra Sings for Only the Lonely-1958-Another heartbreaking album of “saloon songs,” as Sinatra liked to call them. Featuring arrangements by Nelson Riddle, this album includes perennial Sinatra concert favorites “Angel Eyes” and “One For My Baby (And One More for the Road)”. 

Come Dance with Me!-1959-Sinatra’s second album with Billy May, this is a real groovy swinger of an album, featuring such cookin’ tracks as “Too Close for Comfort,” “Saturday Night (Is the Loneliest Night of the Week)” and “The Song is You.” Closes with the terrific tune “The Last Dance,” written for Sinatra by Sammy Cahn and Jimmy Van Heusen. 

Ring-a-Ding-Ding!-1961-Sinatra’s first album for his record label Reprise, this was the only time Sinatra worked with arranger Johnny Mandel. Features the exuberant title track, a Cahn/Van Heusen commission, and great readings of “Let’s Fall In Love,” “A Foggy Day,” and “The Coffee Song.” 

Sinatra/Jobim: The Complete Reprise Recordings-Frank Sinatra recorded two albums with the Brazilian singer/songwriter/guitarist/godfather of bossa nova Antonio Carlos Jobim that are among my favorite things he ever did. The first album with Jobim was 1967’s “Francis Albert Sinatra & Antonio Carlos Jobim.” The second album, recorded in 1969, was never issued in full at the time, with 7 of the 10 songs surfacing on 1971’s “Sinatra & Company” album, and it wasn’t until 1995 that all 10 of the songs were issued. This 2010 album is a bit of a cheat, since it is a compilation, but it’s not a best-of, it simply collects the 1967 and 1969 sessions onto one CD. The 1967 sessions were arranged by Claus Ogerman, the 1969 sessions by Eumir Deodato. I wish Sinatra would have recorded 10 albums with Jobim, but we’ll have to settle for these two.

Sinatra and Sextet: Live in Paris, 1962-Not released until 1994, this gig from Sinatra’s 1962 world tour is simply wonderful, as Sinatra swings with an exuberance seldom heard. He was suffering from a cold at the time, but that really doesn’t matter, it’s still a terrific record.

Frank Sinatra with the Red Norvo Quintet: Live in Australia, 1959-Unreleased until 1997, this concert with vibraphonist Red Norvo is even more swinging than the 1962 Paris concert. It’s really a shame that Sinatra never recorded in the studio with Norvo, or with a similar small group. If I had a time machine, this is one of the Sinatra concerts I’d attend.