1. Dirty Dancing. Robbie is a snobby asshole who refuses to take responsibility for impregnating a lower class girl, saying that "some people count, some people don't". Right after this he tries to lend the main character The Fountainhead unprompted, only temporarily of course, since his copy of the book includes notes in the margins.

2. Lost. Sawyer is a selfish conman (at first) and is shown reading The Fountainhead. To be fair though, Sawyer is shown reading lots of books, so it might not necessarily mean anything.

3. Spider-Man. Spider-Man's co-creator Steve Ditko was an objectivist, and this was reflected in the way Peter would behave in some early 1960s stories, he would often be quite rude and abrasive to others, especially when Peter went to college. As a reference to this, some stories have humorously established that Peter went through a phase of being into Ayn Rand back in college, which he is now embarrassed by.

4. Alternate universe Peter Parker from One More Day. Spider-Man runs into an alternate universe version of himself that never gained spider-powers, and he's a fat videogame developer who is depicted as a loser unhappy with his lot in life, we first see him reading Atlas Shrugged. 

5. Deadshot and the Joker. The Joker is shown reading the Fountainhead, which he calls a knee-slapper, while Deadshot, a contract killer, says that it's one of his favorite books.

6. The Ayn Rand School for Tots in the Simpsons. As you can probably guess, it's a horrible place. Maggie breaks out in a Great Escape parody.

7. Bioshock. Andrew Ryan and his whole failed society is a blatant reference to the many problems with Ayn Rand's philosophy.

Asshole characters are into Ayn Rand