Songfacts®:

• Recorded with his bluegrass backing band the Steep Canyon Rangers, "Caroline" is the first single from Steve Martin's The Long-Awaited Album. A comedy number (his forte), the song is about a rather delusional guy who can't quite get over Caroline despite his hapless attempts to find another just like her. He's already anticipating his next failure:
  
  If I have a drink with someone
  I will tell her all about you
  That will be the big mistake
  That I will make on my first date
• Cecily Strong of Saturday Night Live plays Caroline in the video, which was directed by Brian Petchers. The doofus narrator is Bill Hader, who also spent time on SNL. He looks on helplessly as she flirts with their waiter and takes up with a series of other guys.
• As he would a comedy bit, Martin refined the song over time, working on it in soundchecks and rehearsals.
• Peter Asher produced the album. Known for his work with James Taylor and Linda Ronstadt, Asher also produced Martin's albums with Edie Brickell. In a Songfacts interview, he said of the Steep Canyon Rangers: "They are terrific musicians and have a more profound knowledge of bluegrass than I do, and it's a fairly constrained tradition. But, at the same time, we wanted to push it slightly out of the bluegrass range. It's a big difference between the albums I did with Steve Martin and Edie Brickell, which are not bluegrass records, where I did use all kinds of different musicians on different tracks for different effects."