Molly Ringwald – The Pick-Up Artist (1987)

Molly Ringwald was the quintessential ‘80s girl. She starred in more classic movies of that era than any other starlet and she burned up the screen doing it. The Pick-Up Artist doesn’t have the cult status of The Breakfast Club or Sixteen Candles but it’s a must-see for ‘80s cinephiles. And of course, Downey is at his charming best throughout as a smooth ladies’ man.

Uma Thurman – Johnny Be Good (1988)

Downey stars alongside another couple of ‘80s movies' fixtures here in Anthony Michael Hall and Paul Gleason. As for Thurman, she actually plays Hall’s love interest while Downey is merely the wisecracking sidekick to Hall’s leading man. Nevertheless, Thurman makes the list by virtue of two facts: 1. Both she and RJD are in this movie. And 2. She was possibly the hottest up-and-comer of 1988.

Moira Kelly – Chaplin (1992)

His stunning performance in Chaplin earned Downey an Oscar nomination. After some lean years, our boy went on to once again become the toast of Tinseltown. The same cannot be said of Moira Kelly, who made the move to TV after her big screen career floundered in the ‘90s. Nevertheless, Kelly turns in a great performance in Chaplin and proves exactly how hot she is with a topless scene.

Heather Graham – Two Girls and a Guy (1997)

The world got to know Heather Graham as Rollergirl in Boogie Nights but few people will remember this film from the late ‘90s. Graham is every bit as attractive here as one of Downey’s two love interests.

Calista Flockhart – Ally McBeal (2000-2002)

Downey kicked his climb back to the top of the acting world into full gear on the hit show Ally McBeal at the turn of the century. Of course, Calista Flockhart played the titular character. In the age of curvaceous hotties like Beyoncé, Kim Kardashian, and Christina Hendricks, it’s sometimes hard to remember that ultra-thin girls were once in vogue. Thankfully those days are over.

Gwyneth Paltrow – Iron Man (2008) & Iron Man 2 (2010)

Mrs. Coldplay got herself a plum gig as Tony Stark’s assistant Pepper Potts in the Iron Man movies. Opinions tend to be split on Paltrow’s hot factor but these days she is probably the leading lady most closely associated with RJD thanks to the overwhelming success of these comic book adaptations. She’s on the list, but if you have a bone to pick with that, let us hear it in the comments section. And while you’re at it, tell us who else we missed.

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