1. Ride the Divide (2010) - This is the documentary that essentially got me in to cycling. It follows a group of cyclists as they ride the Continental Divide: the 2700 mile back-roads and mountain trails from Canada to Mexico. This is not a Red-Bull-style scenery and show-off documentary - it follows the emotional and physical trials the group endures, the relationships they form, and the obligations they struggle to meet with their at-home families, during this incredibly challenging, almost month-long ride. The aspect of the documentary that was truly life-changing for me, was the focus on the only female cyclist in the group, Mary Metcalf-Collier, who struggles through some pretty heinous physical set-backs at the beginning of the trip and ends up being the first female to ever finish the race. ONLY ABOUT 100 CYCLISTS have ever finished! It's inspiring to newbies that there are still, even today, races that women have yet to finish or win - still so many ways to explore the world on your bike and make an impact!
(One note: while Mary's story was inspirational, there is a storyline about one of the male competitors which is somewhat infuriating - the guy leaves his 8-months pregnant wife at home so he can do the race, just hoping he can finish before the baby is born. When asked if he feels bad he says, "well, while I'm on this journey, she's on a journey of her own..." It's cringeworthy how egotistical competitors can be, not to mention the gender politics at play here)
(One more note: there is a "follow-up" to RTD called "Reveal the Path" that is not nearly as engaging. It follows many of the same guys as they traverse the globe on their bikes looking for, I don't know... the meaning of life? It's entirely self-indulgent with no plot except to throw the guys into remote areas and watch them ride. And yes, the guy with a now-newborn is in it.)
2. Rising from the Ashes (2012) - This is essentially Cool Runnings for cycling. Lead by a disgraced American cyclist (the first American to compete in the Tour de France and blackballed after an affair with a minor), a group of 5 exceptional Rwandan athletes are picked to begin the daunting task of representing their country as a cycling team. Daunting because pragmatically, the country is poor and the cycling gear and resources scarce. Some of the young men had barely ridden a bike before, and if they had, the bikes were 20+ years old! And daunting emotionally, as the young men are survivors of the Rwandan genocide of the early 90's, many of them losing more than half of their families, but finding some solace in the scenery of a long ride and the joy of an unexpected victory. The men make it clear that they want Rwanda to be seen for the beautiful country it is, and for Rwandans not to be judged as broken and violent, but whole and at peace, and they set out to do this by traveling the world as a cycling team.
My favorite part is when, after they have had quite a bit of success in some African races and in their training, they first come to America to race some semi-pro circuits. Afterwards, they are just completely ravaged. The coach says to the camera that the Rwandans have never seen cyclists ride so fast before. The guys just don't even have the words for it. After the race, when they are sweaty and exhausted, all they can do is smile and shake their heads - but not that snarky, I'll-get-them-next-time type of smile - a genuine, humbled, awe-struck, good natured smile and laughter. It made me absolutely fall in love with them!
After following their ups and downs, the documentary climaxes with a series of Olympic time-trials that require the men to work together for strategy, but also pits them against each other for the final qualifying spots. It basically comes down to two men from opposite Rwandan tribes - the two tribes waring against each other during the genocide. What happens between these two men in the qualifying rounds is shocking, tear-jerking, devastating, joyful and redemptive all at the same time. It's a MUST WATCH!
3. Triplets of Belleville (2003) - Animated but intended for an audience of all ages, this is the sweetest cycling story that is perfect for family movie night or cyclist date-night. A sullen little boy is raised by his grandmother who just wants him to be happy. After some snooping, she discovers the key to his happiness seems to be bicycles. She buys him a bike and he is elated... fast forward (through lots of hilarious scenes of grandma "training" him by blowing a little whistle to keep pace) to him a young adult aspiring to enter the Tour de France.
The movie is filled with such intricate details and tounge-in-cheeck references to the cycling lifestyle that only an animated film could represent so colorfully: like when grandma is feeding her now-adult grandson right before a race and he is seated upon a scale that ticks heavier with each bite. Simple, but so engaging.
When the grandson finally achieves his goal of racing professionally, grandma discovers some sort of cycling mafia that seems to be controlling the races and prohibiting him from winning. And then - poof! - grandson disappears. Afraid he's been kidnapped by the cycling mafia, grandma enlists the help of The Belleville Triplets, a bizarre, defunct singing group, to help save her grandson. It is a weird little dark twist, but beautifully done.
There is one other unique TWIST that I will let you discover on your own. I didn't even REALIZE it until about ten minutes in, so let's see if it takes anyone else longer!