Kind of amazing what he accomplished. Didn't realize his first huge win was on Winning Colors in the Derby. Rode so many great horses in great races, then to come back and get Oxbow, Mucho Macho Man & Beholder, very wonderful for him. Wish him the best.
Can't leave out Rock Hard Ten!
He was also quite good in Seabiscuit and the HBO miniseries Luck. I hear people say he was a jockey so he was just playing himself, but good acting is a great deal more difficult than that. He was especially good in Luck and it's a shame that series was cancelled. Nick Nolte was perfect as the grizzled old trainer who finally lands "the horse", but Gary played his role superbly as well.
Luck was the best. I loved it. Every character was so authentic. I have it all on dvd and I do the marathon watching every few months. The music and the filming was so perfect. HBO had Luck and Deadwood which both were so well-done and so terrific and unfortunately both gone.
I liked Deadwood too! Timothy Oliphant was great in it. By the third season it started losing steam though. I've never asked before because I assume everyone on this site has seen Let It Ride, but I thought it was hilarious. All the characters were a bit over the top, but it still captured a lot that is true about horseplayers.
BTW, one of the best racing movies I ever saw was Casey's Shadow. It was supposed to be based on the Romero's. Randy is in the Hall of Fame (it did take a while though). Who's better than Walter Matthau? He was perfect in the movie.
They are right now filming the Deadwood movie with all of the same characters because it ended so abruptly. It will out next year and I can't wait. Let it Ride is a classic and absolutely the funniest ever! He was having "quite a day!" But out of them all, Luck was magnificent.