I've been a fan of almost all of the documentaries in ESPN Films' 30 for 30 series. While the 30th anniversary has passed, ESPN continues to release documentaries that had originally been planned, and they continue to be of extremely high quality.
"Charismatic" is the story of both the horse and its jockey, Chris Antley. Chris Antley was an extremely talented jockey who had battled substance abuse throughout his career. The kind of talent that is now completely gone from American horse racing in my view. I especially remember Chris Antley, as his first Kentucky Derby win aboard Strike The Gold was the first Derby winner I ever picked. Charismatic was an underachieving horse that became one of the biggest upset winners of the Kentucky Derby, and had a chance at the Triple Crown before breaking down in the final furlong of the Belmont.
Like most of the 30 for 30 documentaries, the subject matter transcends sports and is a human interest story that delves into real human drama. It was directed by Steven Michaels, son of legendary sportscaster Al Michaels. I highly recommend it, and you can watch it on Youtube here: http://www.youtube.com/watch?v=bVY9M3Gyfmo
While we're at it, here's my favorite race call ever, featuring an exciting finish between two legends in turf racing and a roaring crowd: http://www.youtube.com/watch?v=3sfUKPLowpM