Cannibal the Musical by far. That's the only DVD I have that I've watched at least as many times with commentary as without.

Here are some I have listened to more than once...
o Rob Reiner on This is Spinal Tap (Criterion)
o Harry Shearer, Michael McKean, and Christopher Guest on This is Spinal Tap (Criterion)
o Derek Smalls, David St. Hubbins, and Nigel Tufnel on This is Spinal Tap (MGM)
o Bruce Campbell, Sam and Ivan Raimi on Army of Darkness - Director's Cut (Anchor Bay)
o Bruce Campbell on Evil Dead (Anchor Bay)
o Sam Raimi on Evil Dead
o Bruce Campbell and Sam Raimi on Evil Dead II
o Mike Myers and Jay Roach on Austin Powers films
o David Fincher on Fight Club
o David Fincher, Brad Pitt, and Ed Norton on Fight Club
o Chuck Palahniuk and Jim Uhls on Fight Club
o Isolated music score/commentary w/ Danny Elfman on Pee-Wee's Big Adventure
o Any Kevin Smith or Terry Gilliam commentary

Criterion Seven Samurai's good. I like Heston's commentary on Ben Hur, for those that haven't seen it, it's one of those deals that he does not talk through the whole movie, but there's an icon one can click to forward to the next commentary section, the setup assures very little dead time or babbling.

The following commentaries are very funny, almost gut-bustingly hilarious at times but not the most educational in the world (although you'll learn a lot about studio politics and raising money):

Mallrats - Kevin Smith, Ben Affleck, Jason Lee, Jason Mewes, Scott Mosier, Vincent Pereira - one of the best and the funniest, watch out for Lee's Jeremy London impression and the constant Affleck-bashing, running gags include the appearance of Walt Flanagan and Smith's use of colorful backgrounds, also has video via multi-angle

Clerks: The Animated Series - Smith, Mewes, Mosier, Dave "Thanks for watching!" Mandel, Brian O'Halloran, Jeff Anderson, and Chris Bailey - also very funny, especially given the bad rap this series has gotten from network brass, the ideas for additional episodes (discussed during episode 5) are very funny, especially the KITT episode

Kentucky Fried Movie - John Landis, Robert K. Weiss, Jerry & David Zucker, and Jim Abrahams - as a fan of Airplane, The Naked Gun, and The Blues Brothers, this was like a reunion of old friends, Weiss and Landis make some comments that make me laugh out loud especially Weiss' "I think we had a deal with Samsonite" comment during the Fistful of Yen segment

Now for some more scholarly commentaries:

Armageddon - Michael Bay, Jerry Bruckheimer, Ben Affleck, and Bruce Willis on one; John Schwartzman, Ivan Beckey, and Joe (?) Allen on the other - these are very good, Bay and Scwartzman go very in depth regarding technical aspects of the production and it irks me everytime to hear Bay say "7 year olds come up to me and tell me this is their favorite movie"...of course it is, they're 7!

Star Trek II: The Wrath of Khan - while Nicholas Meyer does contradict himself a few times, this is a very smart and eloquent track from one of Trek's great writer/directors

The Abyss - text commentary by Van Ling - the best text commentary there is, just as good as an audio commentary, extremely well written and researched (Ling was a research assistant on the film)

Ghostbusters - Ivan Reitman, Joe Medjuck, and Harold Ramis - this is the first commentary I've ever heard and one of the greatest, very funny and very informative, we learn almost the entire story of the film from concept to completion, uses the subtitle track for MST3K-style sillhouettes (sp?)

Back to the Future trilogy - Q&A sessions with Bob Zemeckis and Bob Gale - these don't run the entire length of the films (BTTF 3 is only 30 minutes or so) but are extremely interesting and educational and they cover everything from writing to visual effects to the actors to the music...I only wish Spielberg would sit in for these types of things but that's another topic altogether

My favourites:

Francis Ford Coppola: The Godfather trilogy

David Bordwell: Alexander Nevsky (Criterion)

Quentin Tarantino: True Romance. He NEVER shuts up on this track! Even when he says he just going to watch the scene, he starts up again after only a brief pause.

Paul Verhoeven, Ed Neumeier, Jon Davison: RoboCop (Criterion)

Roger Ebert: Citizen Kane

Terry Gilliam: Brazil (Criterion)

Chris,

You can find more choices in this thread.

Most of my favourites are already metioned here, but the Hunter Thompson commentary on the Criterion Fear and Loathing is fantastic. Definitely worth a listen.

The Thing with John Carpenter and Kurt Russell. Most JC commentaries are pretty informative, but this one takes the cake!

The In Crowd. Those chicks are as ditzty in real life as they are in the movie. Hilarious.

The Jackass The movie commentaries are hilarious and the Peter Jackson commentary on the Extended Edition of Fellowship of the Ring is very informative and never dull.

-Dean-

The cast commentary on Boogie Nights is fascinating. PT Anderson's solo commentary on the same disc is just as interesting, although probably shouldn't be watched with children around. That guy sure does like his "f-words".

ShaunS

i was scrolling down this thread thinking to myself "i cant believe nobody has mentioned boogie nights!" and shaun mentions it in the last post. i think the pt anderson commentary is one of the best ive heard. but on the criterion laserdisc, his commentary on the john holmes documentary is worth the price of the disc and a ld player, if you dont already have one. hilarious!

CJ

Roman Polanski for THE NINTH GATE and any commentary by John Frankenheimer who goes into a lot of technical detail which is ideal if you want to know more about the film making process. I've bought some Frankenheimer titles just so that I can hear his commentary.

Just to toss a couple of *fun* ones into the mix:

THE FIRST NUDIE MUSICAL and BEGINNING OF THE END

both with Bruce Kimmel, latter with Susan and Flora Gordon (Bert I. Gordon's sife and daughter); former has THREE commentaries, including one for the brand new documentary.

Atom Egoyan and Russell Banks on The Sweet Hereafter: A very good complement to this movie (one of 90's best IMHO). They discuss the movie in depth, the plot, the difference between the book and the movie (and why),... They really help you appreciate the story more by discussing the story, the character motivations and so on.
Not by providing "definite" answers, but by giving hints to find "your" answers to the movie.
The only commentary I've listen to twice ! Fascinating !

Cheers,

Vincent

I always always enjoyed the commentary for The Usual Suspects.

Also, the commentary for Speed (the Five Star Edition) was very, very funny. I think it was the writer and the producer.

I also have to second the Armageddon choice, absolutely hysterical.

"Who's the best espresso maker in Manhattan?"

Weird Al Yankovic's commentary for UHF is great. Even funnier are the handful of visual gags thrown into the commentary (those who have seen the disc know what I'm talking about).

Ben Affleck on Pearl Harbor (with Josh Hartnett).

The sure sign of a good commentary is when, half way through, they say, "There's no way they're going to use this commentary on the DVD..."

One of my favs is definitly the commentary with astronaut Jim Lovell and his wife on the Apollo 13 dvd. Their is nothing like listening to a guy who actually lived through that experience for real! Great stuff, and quite moving too at times.

And no mention of the group commentary on The Goonies dvd yet!? Those are the most fun because it's the whole cast getting together after years and just having a good ol' time reflecting.

I also like the cast commentary on the Final Destination dvd, fun stuff.

And yes, Ben Affleck kills me on the commentary for Armageddon! Especially whenever he makes fun of Billy Bob Thorton from Sling Blade

"mmm hmmm, were gonna send ya up in a spaceship mmm hmmm."

The commentaries on LOTR are very good -- especially the cast commentary and the artist/designer commentary.

Hands-down best commentary I have ever heard, however, is the Spinal Tap "in character" commentary. I wish more classic comedy movies would do this sort of thing.

The commentary with tilly, the voice actor of Chucky & the screenwriter re "The Bride of Chucky" is downright hilarious.

The cast, Susie Bright (the lesbian sexpert),
and Wachowski brothers

(of The Matrix)

on the

BOUND DVD

Insightful, funny and entertaining!!!

Mark

The Rock (Criterion) - mostly because of what Nic Cage contributes

Ronin - Frankenheimer, nuf said

True Romance - QT's commentary and Brad Pitt's mini commentary which is a great lesson for actors in a small part

Kingpin - Farrely brothers: so many stories about where jokes came from

Scream - Wes Craven and Kevin Williamson

Glengary Glen Ross - Alec Baldwin's mini commentary

The Usual Suspects

-Reagan

One of the best commentaries I have listened to is David Morrell's commentary on the First Blood DVD. Morrell wrote the original novel that the movie is based on. He gives comparisons and contrasts between the book and the movie.

The author sheds insight on why he wrote the book, on the character of Rambo, and the making of the original film and all the various challenges and pitfalls that took place. I gain not only insight about the film, but insight on the process of writing. I have listened to the commentary a couple of times and get something new out of it every time. Not only that, but Morrell isn't pretentious about his work.

I love the commentary by Kurt Russell and John Carpenter on the Big Trouble in Little China DVD. At times, the commentary meanders, but they both seem to be terrific friends who really enjoyed making the film. They both talk about what they were trying to accomplish with the film and why some people didn't "get it."

Finally, I have to mention the commentary by Quentin Tarantino on the True Romance SE DVD. It really would have been nice to have had this sort of commentary on "Pulp Fiction'", "Jackie Brown", or "Reservoir Dogs". It is a great commentary that gives insights to the early years of Quentin in the film business as well as what he'd originally intended for the film. Very informative and entertaining.