Probably my favorite documentary ever, this is a fascinating look at the lives of two Chicago kids, Arthur Agee and William Gaines, both with NBA dreams, and the often cold realities when those dreams fall short.  The two families gave the filmmakers tons of access for five years as they captured the ups and downs of the boys’ high school careers, both on and off the court. It’s also a sobering look at what life was like for inner city families in early 1990’s Chicago. The movie is long (almost 3 hours) but is well-paced and I’ve watched it like 20 times. Admittedly that says a lot about me.  But whatever.

Billy Crudup, Monica Potter and Donald Sutherland star in this biopic of Steve Prefontaine, the American 5,000 meter runner from Oregon who died in a car crash in 1975.  Much better than 1997’s “Prefontaine,” this is a thoroughly entertaining film and Crudup is excellent in the lead role. Sutherland is also great as Prefontaine’s track coach Bill Bowerman, who was the co-founder of Nike. I’m not sure why Crudup and Potter didn’t become bigger stars.  Anyone have a theory?  Anyone?  Bueller?

This 1976 classic stars Billy Dee Williams, James Earl Jones and Richard Pryor as a barnstorming black baseball team.  Hilarious at times (I did mention Richard Pryor is in it, right?), touching at others, the best part is the chemistry between the actors who are all having a great time. One of the most underrated baseball movies of all time. I would say that it really captured the spirit of the Negro Leagues, but since I’m a white guy born at least 10 years after they were history, that would be a fairly silly thing about which to try to have an opinion.

Probably the funniest sports movie ever made, Paul Newman is at his best as the player/coach of a minor league hockey team desperate to increase ticket sales any way possible. Enter the Hanson Brothers, the dirtiest players in the league, and the fans love it.  There are at least 5 laugh-out-loud scenes, and if you haven’t seen it, you really should. Directed by George Roy Hill (director of The Sting and Butch Cassidy & the Sundance Kid), this really captures the feel of the 70’s, and even though it wasn’t a huge hit, it obtained cult classic status years later.

Directed by Dana Shapiro (who I went to Camp Lenox with, in case you were curious), this 2005 documentary tells the story of physically disabled athletes playing wheelchair rugby leading up to the 2004 Paralympic games. Super intense, not at all overly sentimental (as you might expect from a movie about disabled athletes) and brilliantly shot and edited.  It was nominated for an Oscar and won Best Documentary Feature at Sundance.

Maybe my favorite of the brilliant 30 for 30 films, this documentary takes a look at why so many professional athletes end up in financial peril despite the millions of dollars most of them make.  It’s incredible to see how unprepared many football, basketball  and baseball players are for the realities of life as a professional athlete.  This film is fascinating and immensely entertaining at the same time. Somehow it seems perfectly reasonable that someone making $20 Million Dollars a year can blow it all on houses for the families, groupies, horrible investments and jewelry. 

This documentary is the story of the Rumble in the Jungle, the 1974 fight between Muhammad Ali and George Foreman.  It seems strange now that Foreman was such a big favorite, but this was one of the biggest boxing upsets of all time.  Ali was such a charismatic figure of course, and the bonds he forms with the locals are inspiring.  Plus, it’s really interesting to see George Foreman playing the villain, especially considering the cuddly, grandpa-like, grill-selling persona he evolved into twenty or so years later.

Gabe Kaplan is the coach of a basketball team that includes the great Bernard King and a girl pretending to be a guy (named Swish).  Nobody in Hollywood is making this movie today, clearly.  Really fun flick though. The basketball scenes are pretty authentic (helps to have an NBA legend on the floor) and Gabe Kaplan is one of the most underrated actors of the 1970’s.  Plenty of stuff to offend you if you’re so inclined.  So that’s a smile.

Michael Lewis’ brilliant (and widely misunderstood) book about Billy Beane and the 2002 Oakland A’s sure didn’t seem like a potential movie when it was released, but they did an incredible job bringing this story to the big screen.  The dialogue is excellent (as expected when Aaron Sorkin is involved) and Brad Pitt and Jonah Hill give standout performances.   A ton of baseball purists hated the book (and it’s utterly shocking how many of those same purists admit they didn’t actually READ the book) and the movie does a tremendous job bringing color to the seemingly dry world of baseball statistics.

Julius (Dr. J) Erving stars as the best player on a bad basketball team that turns to astrology to improve the team’s fortunes. Total cliché, right?  Stockard Channing plays the astrologer, which doesn’t exactly fit hand in glove with her roles as Rizzo in Grease or Abby Bartlett on the West Wing. Most people don’t realize that this was actually a true story, based on the 1970 New York Knicks.  Well, no, not really. Honestly the movie is fairly dated, but it’s a lot of fun.