Songfacts®:

• Most people think they have Vonda Shepard's "Don't Cry Ilene" figured out. Most people are wrong. The singer explains in a Songfacts interview:
  "Yes. There was a real Ilene. And you know what's funny, it is like documented fact that the song is about an interracial relationship; that's not true at all. I don't know who made that up. It's not about that. It cracks me up, because people say it, like, you know, very educated, interesting smart people think that's what it's about."
  
  So what is the song really about? Shepard says it was inspired by a guy she was "kind of in love with" who already had a girlfriend. (Here's the full Vonda Shepard interview.)
• Vonda Shepard got her first taste of fame when she appeared on the hit "Can't We Try" with Dan Hill in 1987. This led to a deal with Reprise Records, who released her debut, self-titled album in 1989. "Don't Cry Ilene" was the most popular song on the set, getting some airplay on Adult Contemporary radio and a few spins on VH1. She parted ways with Reprise in the mid-'90s, but emerged on the pop culture landscape in a big way when she got a regular role on the show Ally McBeal, which ran from 1997-2002. "Don't Cry Ilene" remained a staple of her live shows and appears on her 2012 acoustic set, Solo.