1966 · Album
That’s Life
Arranged and Conducted by: Ernie Freeman · Notable Track: That's Life (top five hit) · CD Reissue: October 1986
Sinatra Swinging Back When Rock Ruled
A reminder that Sinatra could still land a hit on his own terms, even as the charts belonged to someone else.
By 1966, Frank Sinatra was swimming against the current. The Beatles, the Rolling Stones, and a dozen other bands had taken over the radio, and a singer of Sinatra's generation was supposed to fade gracefully into the background. Instead, he made That's Life (1966) — an album built almost entirely around a single track that proved he hadn't lost his grip on what made a song stick in your head.
The title song is the reason this record exists at all. It's a clever, propulsive number about rolling with the punches, and it climbed into the top five despite everything working against it. Ernie Freeman arranged and conducted the studio orchestra with enough snap to make the whole thing feel contemporary without sounding forced or desperate to be young. The rest of the album doesn't have quite the same pull — it's solid material, but the energy that makes the title track work doesn't carry through uniformly. You get a sense that this was built around one great song rather than a collection of songs that happened to find one great moment.
This is a specific kind of album: a late-career record anchored by a genuine commercial success. It's not a masterpiece, and critics haven't treated it that way. But it matters because it happened at all — proof that Sinatra could still command attention on the charts when the odds said he shouldn't be able to. If you're curious about how he navigated the mid-1960s, or you want to hear what a top-five hit sounded like when rock music had supposedly ended everything that came before, it's worth the time.
