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I'd go with...
1) Small Potatoes: Who Killed the USFL?
I would have loved it, even if it was a 10 hour documentary.
2) The Two Escobars
3) The Legend of Jimmy The Greek
Honorable mention would go to 'No Crossover: The Trial of Allen Iverson'
I love what Steve James did with 'Hoop Dreams', so I had very high expectations for this one. It was solid, but I'd be lying if I said I wasn't a bit disappointed with how it all turned out. Something was missing from it, Allen Iverson interviews for sure, but even more than that. It's still good though.
I didn't like 'Silly Little Game', 'Kings Ransom' (what's with all the useless montages?), and especially 'Winning Time': Reggie Miller vs. The New York Knicks. 'SLG' and 'WT' were just too kooky and fun to be relevant.
The one I most want to see, but haven't is 'Into the Wind' b/c I'm curious to see what Steve Nash (director) came up with.
I'd also like to mention the other 30 for 30 that wasn't made.
Bill Simmons had mentioned it on his PodCast, and it was the one about the Aussie who trains boxing kangaroos. He got so full of himself, that he didn't spend enough time training his kangaroos, all of which ultimately lost all of their matches. He was too preoccupied with going on forums, and mocking people who broke T&C's, and proving that the customer is/was always wrong. He'd spend half of the time sniffing the top tiered people's butts, and spend the other half doing his best to wipe out anything under their level. The problem was, he always got away with it, because he knew how to work the system. He'd thank the right person at the right time, so when it comes time to cleaning house, he'd always be innocent.
It's a very moving story, and unfortunately, because he was never taught a lesson, he did the same thing over and over and over again. The sad part, is that his kangaroos never even had a chance to compete. They were out of shape, and never ready to fight.
The producers did everything they could get this documentary 'green-lit', but ultimately, there were too many stipulations (T&C's) to work through.
I hope that they'll make more 30 for 30 documentaries in the future!
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