The Six Degrees of Kevin Bacon

Probably can be done in less but:

Bruce Lee was in Enter the Dragon with Jon Saxton
Jon Saxton was in From Dusk Till Dawn with George Clooney
George Clooney was in Spy Kids 3-D: Game Over with Bill Paxton
Bill Paxton was in Apollo 13 with Kevin Bacon

Peter Sellers (4)

In 3:

Peter Sellers was in Casino Royal (1967) with Woody Allen, Allen was in Sweet and Lowdown with Sean Penn, Penn was in Mystic River with Kevin Bacon

Stellar.

Try this one Kris Kristofferon and then try Alan Tudyk

Kristofferson was in The Jacket with Jennifer Jason Leigh, Leigh was in Road to Perdition with Tom Hanks, who was in Apollo 13 with Kevin Bacon

Try Daz Crawford

Daz Crawford was in Blade II with Wesley Snipes, who was in turn in the fan with Benicio Del Toro , who was in Sin City with Mickey rourke, who was in Diner with Kevin Bacon.

Try James G Stewart.

James G Stewart ( AKA James Stewart ) was in Airport '77 with Jack Lemmon who was in JFK with Kevin Bacon.

Lindsay Lohan

Ok, I got it in 3

1)Lindsay Lohan was in Georgia Rule with Felicity Huffman
2)Felicity Huffman was in Magnolia with Tom Cruise
3)Tom Cruise was in A Few Good Men with Kevin Bacon

haha found this through Google, felt like starting it up again

Kevin Smith.

GO!

Originally posted by Impediment
Kevin Smith.

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Peter Stormare.
Go.

Peter Stormare was in The Big Lebowski with John Goodman.
John Goodman was in Death Sentence with Kevin Bacon.

Russell Crowe.
GO!

Russel Crowe was in Gladiator with Joaquin Phoenix.
Joaquin Phoenix was in Parenthood with Steve Martin.
Steve Martin was in Planes, Trains, and Automobiles with Kevin Bacon.

James Spader.

GO!

James Spader was in Wolf with Jack Nicholson
Jack Nicholson was in A Few Good Men with Kevin Bacon

Will Smith

GO!

Will Smith was in Men in Black with Tommy Lee Jones
Tommy Lee Jones was in The Fugitive with Harrison Ford
Harrison Ford was in What Lies Beneath with Michelle Pfeiffer
Michelle Pfieffer was in The Witches of Eastwick with Jack Nicholson
Jack Nicholson was in A Few Good Men with Kevin Bacon.

Mel Brooks
GO!

Mel Brooks directed The Producers with Matthew Broderick (and provded a line in the film)
Matthew Broderick was in Deck the Halls with Danny Devito
Danny Devito was in Mars Attacks! with Rance Howard
Rance Howard was in Frost/Nixon with Kevin Bacon.

Trey Parker (and/or Matt Stone)

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Trey Parker was in South Park: Bigger, Longer, and Uncut with George Clooney
George Clooney was in Oceans 11 with Brad Pitt
Brad Pitt was in Sleepers with Kevin Bacon

John Cusack.
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John Cusack was in America's Sweethearts with Julia Roberts
Julia Roberts was in Flatliners with Kevin Bacon

Tommy "Tiny" Lister

Go!