There are several really great commentaries I could listen to over and over again. But many of them blend into one after the other. Some of them are fun but disappointing. For example, the commentary for "Jerry Maguire" was fun but wasn't a commentary at all. Almost nothing was said of importance or insight into the movie. Or the commentary for "Y Tu Mama Tambien" was disappointing because all of it was in another language. And a really awful commentary was Carrot Top for "Rules of Attraction", which was crude, not funny and the least insightful or interesting commentary track I've ever heard. But here are some very interesting and insightful commentaries...
Paul Thomas Anderson and Philip Baker Hall - "Hard Eight"
Roger Ebert - "Citizen Kane"
Paul Thomas Anderson - "Boogie Nights"
Ed Harris - "Pollock"
Cameron Crowe - "Vanilla Sky"
Sam Mendes - "American Beauty"
Adrien Lyne - "Jacob's Ladder"
Jill Sprecher - "Thirteen Conversations About One Thing"
Greg Kinner and William Dafoe, Paul Schrader - "Auto Focus"
Spike Lee - "25th Hour"
Steven Shainberg - "Secretary"
Dylan Kidd - "Roger Dodger"
Dustin Hoffman, Jake Gyllenhaal and Brad Silbering - "Moonlight Mile"
Mark Romanek and Robin Williams - "One Hour Photo"
Gus Van Sant and Matt Damon & Ben Affleck - "Good Will Hunting"
Wes Anderson, Owen Wilson and Jason Schwartzman - "Rushmore"
David Fincher, Brad Pitt and Morgan Freeman - "Seven"
David Fincher, Brad Pitt, Edward Norton & Helena Bonham Carter - "Fight Club"