The best of Frank Sinatra: Five essential albums from the iconic singer

The debate likely will rage forever on whether or not Frank Sinatra was a jazz singer. But you’ll get no argument from anyone that Sinatra was one of the greatest performers of modern pop songs, especially those from the 20th century’s Great American Songbook.

Sinatra’s career was so long — spanning seven decades — and his recorded output so vast that it’s hard to come up with his five best albums. It has to be done from a purely personal point of view. But for those who are diving into Sinatra’s catalogue for the first time or returning to some old favourites, you can’t go wrong with these five standout releases.

The Song is You (1994)

When the skinny young Sinatra was singing with Tommy Dorsey’s Orchestra in the early 1940s, records spun at 78 rpm and were made of shellac. The term “album” referred to a book-like package with discs in individual sleeves. So to represent the young Sinatra, I have picked a compilation boxed set that was issued by RCA Victor in 1994 called The Song is You. It consists of five compact discs with material from both studio sessions and broadcast performances. Hear why the bobby-soxers went wild when Frankie sang hits such as I’ll Be Seeing You and This Love of Mine.

Songs for Swingin’ Lovers! (1956)

Sinatra recorded so many classic albums for Capitol with arranger Nelson Riddle’s orchestra that it’s hard to pick just one to represent his style in the 1950s and ’60s. There’s the slow and moody In the Wee Small Hours (1955), also with Riddle’s backing, or Come Dance with Me (1959), which won Grammys that year for both Sinatra and bandleader/arranger Billy May. But for me, the album from that era is Songs for Swingin’ Lovers (1956), which is in the Grammy Hall of Fame and contains Riddle’s arrangement of Cole Porter’s I’ve Got You Under My Skin with that fabulous trombone solo by Milt Bernhart.

Sinatra at the Sands (1966)

Issued on his own Reprise label in 1966, this is Sinatra’s first ever live album. It was recorded during a weeklong engagement in the Copa Room at The Sands hotel in Las Vegas when Sinatra, as leader of the Rat Pack, was a regular in that town. He’s backed by Count Basie and his orchestra with arranger Quincy Jones conducting. Great songs and lively commentary from the Chairman of the Board.

Watertown (1970)

When it was first released on Reprise in 1970, Watertown was not what listeners expected and, as a result, was a bomb with initial sales of only 35,000 copies. It is a concept album centred on a nameless man who tells a heartbreaking story of personal loss because his wife has left him and their two boys for the lure of the big city. The music for Watertown was co-written by Jake Holmes and Bob Gaudio, one of the members of the rock band the Four Seasons. Despite its initial lack of success, Watertown is now considered a forgotten masterpiece.

Sinatra–Basie: An Historic Musical First (1962)

This is a 1962 studio album released on Reprise with music arranged by Neal Hefti. It was the first, but not the last, time Sinatra and Count Basie appeared on a record together. The Basie band is at its best and Sinatra is having a blast as he belts out tunes such as Pennies from HeavenPlease Be Kind and the classic Hefti version of I Won’t Dance. When one of the greatest big bands and one of the greatest big band singers get together, magic happens.

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