Elizabeth Daily.

b. September 11th, 1961.
Elizabeth Daily, aka E.G. Daily, is probably best recognised as Dottie, the long-suffering wannabe girlfriend of Peewee Herman, in Peewee's Big Adventure (1985). This was my very favourite movie when I was ten, and I always felt sorry for Dottie, whose romantic interest in Peewee was rebuffed with all the sensitivity you could expect from an attention-deficit man-child. I had an early "oh my god, it's that girl from that other thing!" moment when I saw Valley Girl (1983) a few years later, where I believe she plays a character who is date-raped - the film is otherwise notable for being one of those teen movies which makes up and attempts to popularise its own slang, and for being the first film in which Nicolas Cage had a starring role.
Daily appeared in several other films during the 80s, such as Ladies and Gentlemen:The Fabulous Stains and Streets of Fire, and also released several pop hits - her single "Say it, say it" made it to #1 on Billboard's Hot Dance Music/Club Play chart in 1986. Check out the hilarious Lolita-themed video clip:

Most of Daily's film and TV roles are now as a voice artist for cartoons - she replaced Christine Cavanaugh as the voice of the little pig Babe for Babe 2: Pig in the City (1998), and is the voice of Buttercup from the Powerpuff Girls, and Tommy Pickles in Rugrats. In terms of live action, she's appeared in recent years in My Sister's Keeper (2009) and in the Rob Zombie horror film The Devil's Rejects (2005), which is where this entry's picture comes from - that film is a veritable who's who of " It's that one guy" moments: almost every minor part is filled by classic horror movie character actors such as Michael Berryman, P.J Soles, Ken Foree, Danny Trejo.
Daily also played Paris Hilton's mom in National Lampoon's Pledge This! (2006). On her website she shares this about the role:

The most ironic part of the whole thing is my x-husband Rick Salomon just happens to be the guy in the infamous x-rated tape with Paris and here I was playing her mom!! Crazy!!! We all ended up having a great time and the cast was awesome!

I wonder if that was awkward, or strange, or anything.