46. The 40 Year-Old Virgin (2005)
As Hollywood studio comedy evolved from gross-out to something slightly more complex, Judd Apatow found himself at the forefront of the movement with his massively successful feature debut.
Of course, there are still plenty of d*ck jokes to be found in The 40 Year-Old Virgin, but the plot is layered with genuine emotion, warmth and even some sentimentality thrown in.
Steve Carrell knocks it out of the park in his first major big screen leading role, with the improv-heavy style generating huge laughs as a raft of razor-sharp comics all manage to leave an impression.