When I was a young child, I would comb through the videos at Hastings for what felt like hours until I had a stack of horse movies I may or may not have seen. Sylvester was one I stumbled across when I was about twelve, which is why I'm using the old artwork for this movie.
It occurs to me now that this movie was probably more than I could handle as a twelve-year-old, because Sylvester is your Cinderella-style horse story surrounded by a crusty Texas attitude. There is cursing, fighting, horse abuse, alcoholism, underage sex in a stall, and attempted rape. However, there is also magical wild horse-girl bonding and totally random western girl turned three-day eventer. And not just three-day eventing. Rolex Kentucky three-day eventing. That's right. She doesn't gradually enter the world of eventing. She makes the jump from working in a stock yard to riding at Rolex.
Charlie is a sixteen-year-old orphan. She takes care of her little brothers in a trailer, breaks horses and rounds up cattle for Mr. Foster's stock yard, and spends a lot of time telling this Matt character to back the hell off already. Matt (Michael Schoeffling of Sixteen Candles and Wild Hearts Can't be Broken) insists that he's going to marry Charlie after she's done with her horse phase, although I'm pretty sure Charlie is unaware of these plans because she's too busy falling for this fleabitten gray--Sylvester. She succeeds at turning him into a cow pony, but he's way too big for the work and eventually her asshole coworker spooks him into jumping a fence and getting both of them fired.
Due to her sudden unemployment, the state is eager to take Charlie away from her brothers and stick her in a typing course. Charlie, not wanting to be a secretary, runs to Mr. Foster, who is drunk and not exactly a logical choice as a safe haven. Her brothers, however, insist on moving in with a drunk (and say so, vehemently) and the choice is made. Mr. Foster suddenly becomes their surrogate father, and has little intention of dropping his Cuervo habit. Around this time, Charlie decides to start jumping Sylvester over anything and everything, upsetting Matt and Mr. Foster for various vague reasons. Why can't she just get married to Matt and stop being annoying? God, life is so hard.
Eventually, Matt realizes that he's not going to get anywhere with Charlie unless he, like, attempts to support her dream of Olympic gold. This method works perfectly, and he's suddenly eating dinner with Charlie's highly dysfunctional, partially drunk, family. Then, all of a sudden, Mr. Foster knows everything that can be known about three-day eventing because he was in the cavalry. So he gives in and starts to mentor Charlie, leading her to her first event, the Rolex.
Granted, she's competing in preliminary, and back then it was possible to do this. Also, this is still obviously absolutely and completely insane. Also, Mr. Foster makes at least one massive disparaging comment about how stupid this plan is, but is bullied into line by Charlie insisting that he's killing her dreams. So they pack up Sylvester and head to Kentucky, where Matt gets pissed if anything male even glances at Charlie and Charlie proceeds to impress just about everyone.
This all comes to a head with Matt and random USET member getting into a brawl in the middle of a cocktail party. Because Texans solve problems with their fists! There's a big issue made out of how Charlie doesn't belong with these people, and how she needs to get Sylvester sold for the sake of her family, but in the meantime has been just so gosh darn impressive she's probably never going to see Texas again.
It's my opinion that she probably doesn't.
That's Sylvester. You pick it up because it's a horse movie, you stay for the crusty Texas alcoholics, no matter how unrealistic the plot.