#1 Breaking Away
#2 American Flyers

After that it's:
Klunkerz (Movie about the birth of mountain biking in California - My hero Tom Ritchey is in it)
The Ride (Re-enactment of the 1928 Tour de France - vintage bikes, gear and all - quite good)
Send It (A bike messenger movie on GCN+ - more of a documentary in the UK)
Quicksilver (Kevin Bacon as a bike messenger)

GCN Plus has some really, really excellent bike movies and documentaries. Worth the price of admission in my opinion and their library continues to build.