Dick is a 1999 teen comedy that showed Ryan Reynolds’ comic potential from an early age. Reynolds started his career with guest appearances on shows like Sabrina The Teenage Witch and The X-Files, before landing a lead role on the cult sitcom Two Guys, A Girl And A Pizza Place, which debuted in 1998. Even at that stage, Reynolds’ natural comic talents were evident and it didn’t take long for movie roles to come along. His first big star vehicle was 2002 college comedy Van Wilder, which also featured an early appearance by Aaron Paul as “Wasted Guy.”

Around 2004 Reynolds was already interested in starring in a Deadpool adaptation, though the movie’s journey to the big screen would famously be a slow one. Instead, his first comic book movie was 2004’s Blade: Trinity, where he easily stole the movie from a clearly disinterested Wesley Snipes. Reynolds always seemed poised to break out in a big way, but major solo vehicles like Green Lantern or R.I.P.D failed to take off. After being trapped in development hell for years, Deadpool finally came out in 2016 and the actor’s rise has been unstoppable ever since.

Ryan Reynolds’ next movie will be Michael Bay’s Netflix action epic 6 Underground. One of his earliest movie roles was an appearance in 1999 cult comedy Dick. This teen comedy stars Kirsten Dunst and Michelle Williams and is a strange comic take on the Watergate scandal. In the film’s version of reality, two teenagers who are hired by Richard Nixon (Dan Hedaya) to walk his dog become instrumental in bringing down his presidency when they learn his true nature.

One key scene of Dick finds the two coming to the home of White House Chief of Staff H.R. Halderman (Dave Foley, Monsters University). To do this, Besty (Dunst) fools Halderman’s dim son Chip - played by Ryan Reynolds - into letting her into the house to make out. While Chip is distracted, Michelle William’s Arlene sneaks in to steal a key piece of evidence against Nixon. Reynolds doesn’t have a lot of screentime in Dick, but his nervous energy and fumbling for words make Chip both delightfully awkward and a little endearing.

Dick director Andrew Fleming (Ideal Home) later revealed Reynolds was cast at the last moment when they couldn’t find anybody else, but that he nailed the role. Reynolds would soon go on to leading roles but Dick was an early sign he was already destined for bigger things.

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