The Many Faces of Paul Rudd (Slideshow)

9. Josh in “Clueless” (1995)

In this classic 90s flick, Rudd plays Josh, the liberal-minded college freshman, who’s also the ex-step brother of main character Cher (Alicia Silverstone). Josh does all sorts of college-y things like, you know, caring about social causes, and reading Nietzsche outside by the pool. Cher might call Josh “granola breath”, and Josh might look down upon Cher for being vain and materialistic, but in the end, the two realize their love for one another.Who could forget their classic staircase kiss at the end of the film as one of the most iconic moments in the world of 90s teen cinema? (Photo by Paramount Pictures)