I'm pretty sure everyone is into bikes as much as I am, with that in mind I'm recommending movies you are sure to love.

Breaking away

Okay, 2 racing teams, the poor townie kids (cutters), and the richie filthy rich college frat boys. Protagonist gets a bike, trains a bunch, races a semi truck on the highway, showdown with frat boys...

Coolest part is that the Greeks vs. Cutters race is real, and the cutters finally won the race in 2005. The movie's Won an Oscar, is the #8th most inspiring movie of all time, and is indisputably rad.

Quicksilver

A hotshot wall street whiz-kid Kevin Bacon quits his high roller day job to become a bike messenger. Includes several scenes with Kev performing bike-ballet on a 1-1 geared fixie with the drops flipped up for bar spins. He basically invents hipster in this movie.

American Flyers

Kevin Costner is pretty cool too. In this one he's riding The Hell of the West. Either him or his brother may or may not have a terminal disease, but they're not really sure. I don't recall either. This one's a tear jerker in a good way.

Others That I mostly Haven't Seen

Loads more here, although many are literally impossible to find. Also it's hosted on GeoCities, soo the site's likely to be gone soon. http://uk.geocities.com/mikstar123/films.html