Best of 1950s: #30 – 21

Frank Sinatra in 1955

As long as there has been “pop” music, there has always been an experimental counterpart to keep the balance. Throughout the 1950s, Frank Sinatra was the chart-topper who set the standard in sophistication. It’s no surprise that he has six LPs in the 100 Greatest Albums of the 1950s. On the other end of the spectrum were avant-garde innovators like Stan Kenton and Cecil Taylor, who pushed the boundaries and tested the very limits of what jazz music was capable of.

30. Thelonious Monk Trio

Thelonious Monk Trio

ArtistThelonious Monk

Genre: Bebop

Thelonious Monk’s dissonant, slightly off-kilter chord progressions are warm and welcoming despite their occasional harsh atonality. Even in this minimal setting, Monk is able to conjure up a surprising world of sound. Thelonious Monk Trio remains one of his defining achievements. Continue reading…

29. Ellington Uptown

Ellington Uptown

ArtistDuke Ellington

Genre: Big Band

Even though Duke Ellington’s best work was made during the 1930s, Ellington Uptown is quite possibly his finest studio album. It’s also his most underrated. Featuring five of his greatest compositions, including the Louie Bellson showcase “Skin Deep” and the 14-minute “Harlem” suite, this LP is a timeless classic regardless of the era. Continue reading…

28. Frank Sinatra Sings for Only the Lonely

Frank Sinatra Sings for Only the Lonely

ArtistFrank Sinatra

Genre: Traditional Pop

When asked if he had a favorite album among his own recordings, Frank Sinatra quickly answered with Only the Lonely. It’s easy to see why. Created during a particularly turbulent period of his life — the disintegration of a toxic marriage to Ava Gardner — the LP is brooding, emotional, passionate, introspective, stoned, intense and vulnerable in a manner that is quite unmatched throughout Sinatra’s career. It’s not only his most committed performance; it’s also his most autobiographical. Continue reading… 

27. The Wildest!

The Wildest

Artist: Louis Prima

Genre: Swing

For Louis Prima and his excitable cohorts, the party never stops. If you don’t think that 1950s screwball humor holds up today, I highly suggest you listen to this exuberant blend of big-band jazz and lowbrow comedy. The Wildest! is easily one of the most fun albums of all time. Continue reading…

26. Innovations in Modern Music

Innovations in Modern Music

ArtistStan Kenton

Genre: Avant-Garde Jazz

Stan Kenton utilizes the full range of his big band “orchestra” like no other jazz musician before or since — from tone clusters that resemble the music of Charles Ives to off-kilter piano chords that predict the experiments of Eric Dolphy, Innovations in Modern Music is one of the most daring jazz releases of all time. Continue reading…

25. The Atomic Mr. Basie

The Atomic Mr Basie

ArtistCount Basie

Genre: Big Band

By 1958, Count Basie’s popularity had waned quite a bit. His live performances were still electric and his tours still successful, but the big-band genre he practically invented had long ago been passed over by bebop and its modernist variants. Basie was past his prime. Or so everyone thought.

At 53-years-old, The Atomic Mr. Basie marks the zenith of the Count’s creative exploration. Not only does it swing; it rocks. And his entire career peaks with the 4-minutes-50-seconds that make up “Lil Darlin” — one of the most satisfying finales of the decade. Continue reading…

24. Charlie Parker with Strings


ArtistCharlie Parker

Genre: Jazz

Charlie Parker had always been interested in classical music, particularly the innovations of Igor Stravinsky, and it had always been his longtime desire to record in an orchestral setting. As one of the first bebop artists to perform in an orchestral setting, Charlie Parker with String is an album that seamlessly bridges genres and cultures — jazz mixes with elements of classical, and the contrast of the string ensemble against Parker’s standalone solos still sounds fresh to this day. Continue reading…

23. Songs for Swingin’ Lovers


ArtistFrank Sinatra

Genre: Swing

Contrasting the solitary torch songs of the previous yearSongs for Swingin’ Lovers is bright and sunny. Instead of the sad, lonely and drunk Sinatra, this is happy, horny and buzzed Sinatra. Frank’s voice never resounded with more confidence or charisma, and it’s his immense swagger that really makes this album swing. Continue reading…

22. Jazz Advance

Jazz Advance

Artist: Cecil Taylor

Genre: Avant-Garde Jazz

Cecil Taylor’s piano runs are a thing of wonder, astonishing in how he conjures up a world of sound — so much sound — in such a short space. One moment he’s playing bebop, the next it’s pure atonal expressionism. Taylor’s music contains more surprises in one measure than most jazz musicians can muster in an entire career.

Jazz Advance is one of the greatest jazz debuts of all time. It’s certainly the most daring. Taylor was already molding the shape of jazz to come before the words “free jazz” even entered Ornette Coleman’s lexicon. This 1956 LP is a wonder of invention — adventurous songcraft that rewrites the rulebook while kicking convention in the balls. Continue reading…

21. Everybody Digs Bill Evans

Everybody Digs Bill Evans

Artist: Bill Evans

Genre: Modal Jazz

Bill Evans’ impressionistic piano style was unlike anything else ever heard in jazz. As Miles Davis put it: “He plays the piano the way it should be played.” Not much else needs to be said; the music speaks for itself. Continue reading…

Top 100 Albums of the 1950s

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