ESPN 30 For 30: One Night In Vegas.
Another impressive documentary in this series, following on from 'The Two Escobars', 'Straight Outta LA' and 'Jordan Rides The Bus'. This one follows the friendship between boxer Mike Tyson and rapper Tupac, upto Tyson's fight in Vegas September 1996 and the drive by shooting which would eventually claim Tupac's life. It features interviews with Tyson himself and a slightly incoherent (isn't he always), but well tailored Mickey Rourke.
I was pretty disappointed in all of those, actually.
Two Escobars because of the filmmaking (they inexplicably stretched 4:3 footage to 16:9, making everyone look fat), it was so hard to watch I didn't even finish it. The Chris Evert/Martina Navratilova one was unintentionally hilarious.
The Birth of Big Air is the only one I've liked for awhile. But
Winning Time is one of the best.