Much like its predecessor, Frank Sinatra's Greatest Hits, Vol. 2 is more effective as a portrait of Sinatra at a particular stage in his career than as a comprehensive collection. Like Greatest Hits, the album mainly consists of pop hits and songs pulled from movie soundtracks, adding in a pair of pop/rock hits for good measure. Although "My Way" became Sinatra's signature song of the '70s and '80s -- primarily because his spectacular performance rescues the clichéd song -- none of these tracks were particularly big hits; several of the cuts are album tracks, while the highest-charting single was "Cycles," which peaked at number 23. While the 11 tracks might not all be hits, they are fairly representative of the sound of Sinatra's music in the late '60s. There's a couple of forgotten gems, particularly the wonderfully moving "What's Now Is Now" and a gorgeous arrangement of George Harrison's "Something," but there is also more dross than the previous Greatest Hits collection. Even with a handful of mediocre tracks, Greatest Hits, Vol. 2 remains an enjoyable sampler, containing several classic Sinatra performances ("My Way," "The September of My Years").
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AllMusic Review by Stephen Thomas Erlewine