Holmes Osborne

Rules Don't Apply 23rd November 2016 as Cappy

Fun Size 24th October 2012 as Mr. Brueder

Larry Crowne 30th June 2011 as David Busik

Disconnect 6th August 2010 as Russell Simmons

Unthinkable 26th May 2010 as General Paulson

The Box 29th October 2009 as Dick Burns

All About Steve 6th August 2009 as Soloman

Southland Tales 14th November 2007 as Senator Bobby Frost

The Comebacks 19th October 2007 as Man in Suit

Meet Bill 7th September 2007 as Mr. Jacoby

Dragon Wars: D-War 1st August 2007 as Hypnotherapist

Air Buddies 12th December 2006 as Selkirk Tander

Walkout 18th March 2006 as Principal Ingles

Dreamer: Inspired By a True Story 10th September 2005 as Doc Fleming

A Lot Like Love 21st April 2005 as Stephen Martin

Confessions of an Action Star 23rd January 2005 as Richard Orchid

Wake Up, Ron Burgundy: The Lost Movie 28th December 2004 as Director

Anchorman: The Legend of Ron Burgundy 28th June 2004 as Director

Cheaper by the Dozen 24th December 2003 as Nick Gerhard

A Carol Christmas 7th December 2003 as Hal

Identity 25th April 2003 as Judge

Waking Up in Reno 13th December 2002 as Doc Tuley

The Quiet American 22nd November 2002 as Bill Granger

Windtalkers 7th June 2002 as Colonel Hollings

Domestic Disturbance 28th October 2001 as Shady Tree Motel Clerk

Living in Missouri 11th October 2001 as Uncle Roy

The Deep End 21st January 2001 as Loan Officer

Donnie Darko 19th January 2001 as Eddie Darko

Bring It On 25th August 2000 as Bruce Shipman

Miracle in Lane 2 13th May 2000 as Randall

Election 23rd April 1999 as Dick Metzler

The Mod Squad 26th March 1999 as Pete's Father

The White River Kid 1st January 1999 as Fergus Kenrod

Affliction 12th February 1998 as Gordon LaRiviere

The Lake 1st February 1998 as Newscaster

How to Make the Cruelest Month 16th January 1998 as Dean Rice

That Thing You Do! 4th October 1996 as Mr. Patterson

Murder Ordained 3rd May 1987 as TV Evangelist

Nice Girls Don't Explode 1st February 1987 as Dick

The Student Body 18th May 1976 as Joe