Currently in the lead: Elijah Wood followed by Hayden Christensen
The list so far... (In alphabetical order by last name)

Ben Affleck [5]
Sean Astin [2]
Michael Ballack
Bobby Barry
Sean Bean
Chester Bennington
Sean Biggerstaff [9]
Billy Boyd [9]
Brandon Boyd [4]
Hayden Christensen [20]
Eddie Cibrian
Kurt Cobain [3]
Chris Cornell [2]
Joseph Cross
Matt Damon [4]
Johnny Depp [2]
Vin Diesel
Jamie Draven
Eminem
Jimmy Falon [2]
Tom Felton [2]
James Franco [2]
Brendan Fraiser [4]
Jay Gordon
Dave Grohl [2]
Jake Gyllenhael
Josh Hartnett [8]
Taylor Hawkins [2]
Joshua Jackson [2]
Daniel Johns
Anthony Kiedis
Ashton Kutcher [5]
Chris Klein
Heath Ledger [8]
John Lennon
Josh Lucas
Ewan Magregor [13]
Toby Maguire [10]
Chris Martin
Dominic Monaghan [7]
Ian McKellen
Viggo Mortensen [5]
Conan O'Brien
Ryan Philippe [5]
Joaquin Phoenix [2]
River Phoenix [2]
Brad Pitt
Brad Renfro
Paul Rudd
John Rzeznik
Andre Schneider
Gregory Smith
Scott Speedman
Rob Thomas
Justin Timberlake [4]
Seann William Scott [2]
Paul Walker [4]
Shane West [6]
Elijah Wood [26]
Thom Yorke
Usher
Yoda [5]