Jeff Bridges (THE FISHER KING, TIDELAND) 7 years before "The Dude", Bridges abided as pony-tailed radio shock jock Jack Lucas who finds redemption by way of a crazy homeless Robin Williams (see end of list). Bridges' fate was less rosy in TIDELAND (2005) - he plays a crusty old rocker reminiscent of Kris Kristopherson (a foreshadowing of CRAZY HEART?) who dies of a heroin overdose and spends most of the film as a rotting corpse sitting upright in a chair in a rustic farmhouse. Also notable: Bridges narrated the excellent heartbreaking documentary LOST IN LA MANCHA that focused on Gilliam's aborted 2000 production of THE MAN WHO KILLED DON QUIXOTE. 
Jim Broadbent (TIME BANDITS [1981], BRAZIL [1985]) The small but juicy role of a sleazy Compere of the game show "Your Money Or Your Life" was one of Broadbent's first film roles. He appeared again in Gilliam's next film, the bizarre but brilliant BRAZIL, as Dr. Jaffe - a plastic surgeon for one of the other notable cast members on this list (Hint: skip ahead 2).
Winston Dennis (TIME BANDITS, BRAZIL, THE ADVENTURES OF BARON MUNCHAUSEN 1988) A couple of bit parts as "Bull-headed Warrior" who battled King Agamemnon (Sean Connery) in TIME BANDITS and "Samurai Warrior" in BRAZIL led to an actual character name for Dennis, actually 2, Bill/Albrecht, an intertwined duo in Gilliam's overblown but still incredibly charming epic comedy: THE ADVENTURES OF BARON MUNCHAUSEN (1988). 
Johnny Depp (FEAR AND LOATHING IN LAS VEGAS, THE IMAGINARIUM OF DOCTOR PARNASSUS, ) A Hunter S. Thompson adaptation is not a characteristic project for the dogged director, but with the demented Depp as the Gonzo journalist, Gilliam found his fantasist footing in the trippy terrain. Depp lent a hand famously filling in for Heath Ledger as "Imaginarium Tony #1" in the upcoming IMAGINARIUM... and is slated to be Sancho Panza (a role he was unable to complete in 2000) in THE MAN WHO KILLED DON QUIXOTE (2011). Barring any unforeseen incident, mind you.Katherine Helmond (TIME BANDITS, BRAZIL, FEAR AND LOATHING IN LAS VEGAS)
While she's best known for her US television sitcom work on Soap, Who's The Boss, and Everybody Loves Raymond, Helmond has an almost alternate reality film career in the alternate realities of Gilliam. In TIME BANDITS she's fittingly named Mrs. Ogre as she's the wife of "Winston the Ogre" (Peter Vaughan), in BRAZIL she's Ida Lowry - the mother of protagonist Sam Lowry (Jonathan Pryce), and in FEAR AND LOATHING... she's "Desk Clerk at Mint Hotel" - a study in uncomfortable disapproving scowling. You'd think she'd be used to Gilliam's grotesqueries by that point.
Ian Holm (TIME BANDITS, BRAZIL) To go from the legendary Napoleon to the lowly office boss Mr. M. Kurtzman in just a few years is quite a demotion. And perhaps it's adding insult to injury that neither role has any positive light shed on them but Holm puts in perfect performances that actually provoke sympathy. Incidentally Holm would go on to portray Napoleon again in THE EMPEROR'S NEW CLOTHES (2001).Michael Jeter (THE FISHER KING, FEAR AND LOATHING IN LAS VEGAS)
Jeter died in 2003 leaving behind an eclectic career that stretched from musical theater to television comedy to the silver screen and back again. His parts in 2 of Gilliam's finest films as "Homeless cabaret singer" and "L. Ron Bumquist" are as memorable as character acting can be - especially when he belts out a medley of show tunes in drag to Amanda Plummer in THE FISHER KING.
Simon Jones (BRAZIL, TWELVE MONKEYS) These are pretty blink and miss them cameos (as an "Arrest Official" and "Zoologist" respectively) from Python pal Jones best known as Arthur Dent on the BBC TV version of The Hitch Hiker's Guide To The Galaxy (1981).
Heath Ledger (THE BROTHERS GRIMM, THE IMAGINARIUM OF DOCTOR PARNASSUS) Of course, the tragic death of Heath Ledger in 2008 deprived the world of an amazing young talent, but a blossoming Gilliam leading man is how he'll remain frozen in time as "Tony" in his last film: THE IMAGINARIUM... Ledger was reported as being close to Gilliam beginning with their work on BROTHERS GRIMM, so it's not so far-fetched to imagine them collaborating often had he lived. Charles McKeown (TIME BANDITS, BRAZIL, THE ADVENTURES OF BARON MUNCHAUSEN, THE IMAGINARIUM OF DOCTOR PARNASSUS)
McKeown has been on hand to fill in random bit player parts in these 4 films simply because he co-wrote them with Gilliam. His work as "Theater manager", Harvey Lime, Rupert/Adolphus, and "Fairground Inspector" may go majorly un-noticed but such a solid player should at least get a shout out from this blogger.
Christopher Meloni (TWELVE MONKEYS, FEAR AND LOATHING IN LAS VEGAS) Before he was Detective Elliot Stabler on Law & Order: Special Victims Unit, or criminal Chris Keller on Oz for that matter, Meloni played Lt. Halperin in TWELVE MONKEYS then "Sven, Clerk at Flamingo Hotel" in FEAR AND LOATHING...
Derrick O'Connor (JABBERWOCKY, TIME BANDITS, BRAZIL) According to Wikipedia: "Terry Gilliam, who has directed O'Connor on three films, has noted in his audio commentaries that Derrick seems to have a habit of taking away most of his dialogue in favor of physical character humor. Notable examples include TIME BANDITS, in which his characters' dialogue was resorted to simple grunts while the Maid Marian character 'translated' for him and in BRAZIL , in which Derrick scrapped all of his character's dialogue and simply repeated the dialogue of Bob Hoskins' character."Michael Palin (JABBERWOCKY, TIME BANDITS, BRAZIL)
Gilliam's former Python mate Palin was his first leading man as Dennis Cooper - dragon slayer in JABBERWOCKY (1977). Palin went on to co-write TIME BANDITS and appear in it as Vincent, who shows up in as Shelly Duvall's lover in 2 different time periods. His last role for Gilliam was as the devious but dapper Jack Lint in BRAZIL. Christopher Plummer (TWELVE MONKEYS, THE IMAGINARIUM OF DOCTOR PARNASSUS)
In TWELVE MONKEYS, the venerable Plummer played Dr. Goines, a world-renowned virologist and father to a crazy radical Brad Pitt. He has a larger role, the title role, in Gilliam's latest offering. In an interview on ClashMusic.com Gilliam spoke of the collaboration: "It’s wonderful trying to create a little family group. At one stage I’m taking Christopher Plummer, one of the greatest actors of a few generations, and having him do these different double acts; one with a model with little acting experience, one with a two-foot-eight man and one with Tom Waits, America’s greatest musical poet. And it all worked out!”
Jonathan Pryce (BRAZIL, THE ADVENTURES OF BARON MUNCHAUSEN, THE BROTHERS GRIMM) As protagonist Sam Lowry in BRAZIL, Pryce provided an ingratiating everyman. He had smaller but still memorable parts in MUNCHAUSEN as "The Right Ordinary Horatio Jackson", and BROTHERS GRIMM as "Delatombe" - a conniving French General. 
Jack Purvis (TIME BANDITS, BRAZIL) A dwarf who appeared in all 3 of the original STAR WARS trilogy, Purvis was Time Bandit Wally, Dr. Chapman in BRAZIL, and Jeremy /Gustavus in MUNCHAUSEN. Unlike his roles as Jawas and Ewoks for Lucas, in Gilliam's films he at least got to show his face and have a few lines. Purvis died in 1997, leaving behind a brief but fascinating filmography.
Peter Stormare (THE BROTHERS GRIMM, THE IMAGINARIUM OF DOCTOR PARNASSUS) The only actor to appear on both Gilliam's and the Coen Brothers' repertory role calls, Stormare is a towering intimidating stonewalling actor who seems to fit into whatever skewed scenario visionary film makers come up with. His roles in these 2 films couldn't be more different: he's the thug "Calvadi" and in BROTHERS GRIMM he's credited as "The President". Well, maybe I have to wait to see if they're really so different.
Verne Troyer (FEAR AND LOATHING IN LAS VEGAS, THE IMAGINARIUM OF DOCTOR PARNASSUS) Troyer, best known as Mini-Me from the AUSTIN POWERS films, seems to be the go-to little person since the original Time Bandits are too old or deceased now. Maybe Gilliam should give Peter Dinklage a call next time out.
Peter Vaughn (TIME BANDITS, BRAZIL) As a medieval creature who complains of a bad back, the Pythonesque "Winston the Ogre" was wonderfully played by Vaughan: "You try being beastly and terrifying... you can only get one hour sleep a night because your back hurts, and you daren't cough unless you want to pull a muscle." In BRAZIL he had a crucial bit part as the ironically named Mr. Helpmann. 
Tom Waits (THE FISHER KING, THE IMAGINARIUM OF DOCTOR PARNASSAS) Waits steals the show in THE FISHER KING as "Disabled Veteran" with a monologue in which he declares: "I'm what you call kind of a "moral traffic light", really. I'm like sayin', "Red! Go no further!" Looks like he may be set to steal the show again in IMAGINARIUM... in what may be the meatiest role on this list: Mr. Nick/The Devil. Also between these 2 roles his song "The Earth Died Screaming" appeared in TWELVE MONKEYS.Robin Williams (THE ADVENTURES OF BARON MUNCHAUSEN, THE FISHER KING)
The wild wacky fast talking Williams looked at the time like he might become a Gilliam mainstay but alas that so far was not to be. In MUNCHAUSEN his manic "King Of The Moon" ("I think therefore you is"), whose head detaches from his body, hurriedly floats off with the movie for a few priceless moments, but it's his touching role as Perry in THE FISHER KING that stacks up there with Williams' best work.Okay! Is there anyone I missed?
More later...
