26. The 40-Year-Old-Virgin (2005)
Another masterpiece from Judd Apatow (director), this is also the film that took Steve Carell (who co-wrote the screenplay) to film star status. While the movie can get a little slow at times, the lead up to Carell’s Andy actually losing his virginity is quite hilarious. Thanks, mostly, to a great supporting cast including Paul Rudd, Romany Malco, Seth Rogan and Jane Lynch. Andy enduring a chest-hair waxing is one of the more memorable scenes in any of Apatow’s films. Watching Rogen, Rudd and Malco try to contain themselves during said scene is even more entertaining.
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