Jonathan Loughran

Jonathan Loughran (born November 3, 1966) is an American character actor, best known for his appearances in most Happy Madison films with Adam Sandler.

Career He is Sandler's long-time friend and assistant, the two having worked together at least 40 times.

He is also known for appearing in a few Quentin Tarantino films, including Kill Bill: Volume 1 (2003) and its sequel (2004), and Death Proof (2007).

Filmography

Sexbomb (1989) as Barry Bulletproof (1996) as Rookie Cop The Waterboy (1998) as Lyle Robideaux Big Daddy (1999) as Mike Late Last Night (1999) as Nitro Little Nicky (2000) as John Undeclared (2001) as Himself Punch-Drunk Love (2002) as Wrong Number The Master of Disguise (2002) as Security Guard Eight Crazy Nights (2002) as Cop #1 (voice) National Security (2003) as Sarcastic Cop Anger Management (2003) as Nate Dickie Roberts: Former Child Star (2003) as Himself Kill Bill: Volume 1 (2003) as Trucker 50 First Dates (2004) as Jennifer Kill Bill: Volume 2 (2004) as Trucker Kill Bill: The Whole Bloody Affair (2004) as Trucker Grandma's Boy (2006) as Josh The Benchwarmers (2006) as Brad's Assistant Coach The King of Queens (2006-2007) as Bobby Death Proof (2007) as Jasper I Now Pronounce You Chuck & Larry (2007) as David Nootzie Get Smart (2008) as Orange Team Guy The House Bunny (2008) as Tall Prostitute Bedtime Stories (2008) as Party Guest Finding Sandler (2009) as Himself Grown Ups (2010) as Robideaux MKC: The Monster Killers Club (2010) as Walt P. The Great Marcusio (2010) as Gil Mobsters (2011) as Jerry Giggles Just Go with It (2011) as Pick Up Guy #1 Bucky Larson: Born to Be a Star (2011) as Bondage Guy Jack and Jill (2011) as Monica's Boyfriend Grown Ups 2 (2013) as Robideaux Blended (2014) as Home Plate Umpire Pixels (2015) as White House Gate Guard Hotel Transylvania 2 (2015) as Cop (voice, uncredited) The Ridiculous 6 (2015) as Rifleman The Do-Over (2016) as Grizzly-Looking Biker Hell's Kitchen (2016) as Himself Sandy Wexler (2017) as Trucker Jon Murder Mystery (2019) as Man at Train Station The Wrong Missy (2020) as Paul Leo (2023) as Animal Handler Happy Gilmore 2 (2025) as Crazy Eyed Orderly