Following the across-the-board success of Strangers in the Night, That's Life continued Frank Sinatra's streak of commercially successful albums that straddled the line between traditional and contemporary pop music. Adding more pop music techniques to his repertoire of show tunes, That's Life made contemporary pop concessions while satisfying Sinatra's own taste for weightier, more respected material. Although it was a pop-oriented record, Sinatra had not begun to rely on rock-influenced productions; instead, arranger/conductor Ernie Freeman contributed charts that alternated between bluesy, brassy swingers and mildly schmaltzy string arrangements, supported by an overbearing backing chorus. While the title track was the hardest blues Sinatra ever tried, that approach wasn't attempted for the entire album. A few tracks -- particularly a rearrangement of the New Vaudeville Band's campy "Winchester Cathedral" and the static version of "The Impossible Dream" -- fall flat, but the album works when Sinatra is either tearing into the song (like "That's Life") or coaxing life out of mid-level ballads like "You're Gonna Hear from Me."
AllMusic Review by Stephen Thomas Erlewine