
Plot
Peter Klaven is a successful real estate agent who, upon getting engaged to the woman of his dreams, Zooey, discovers, to his dismay and chagrin, that he has no male friend close enough to serve as his Best Man. Peter immediately sets out to rectify the situation, embarking on a series of bizarre and awkward "man-dates."
Trailer
Cast

Paul Rudd
Peter Klaven

Jason Segel
Sydney Fife

Rashida Jones
Zooey Rice

Andy Samberg
Robbie Klaven

J.K. Simmons
Oswald Klaven

Jane Curtin
Joyce Klaven

Jon Favreau
Barry

Jaime Pressly
Denise

Rob Huebel
Tevin Downey

Thomas Lennon
Doug

Sarah Burns
Hailey

Lou Ferrigno
Lou Ferrigno

Greg Levine
Hailey's Date

Jean Villepique
Leanne

Kym Whitley
Female Co-Worker

Colleen Crabtree
Female Co-Worker

Caroline Farah
Female Co-Worker

Mather Zickel
Gil

Aziz Ansari
Eugene

Nick Kroll
Larry

Liz Cackowski
Zooey's Friend

Kulap Vilaysack
Zooey's Friend

Catherine Reitman
Zooey's Friend

Carla Gallo
Zooey's Friend

Vicki Davis
Zooey's Friend

Josh Cooke
Alan (Bench Press Guy)

Jay Chandrasekhar
Barry's Buddy

Seth Morris
Barry's Buddy

James P. Engel
Barry's Buddy

Jerry Minor
Berry's Buddy

Joe Lo Truglio
Lonnie (Voice Crack Guy)

Murray Gershenz
Mel Stein

Keri Safran
JAR Waitress

Greg Tuculescu
Open House Couple

Ian Roberts
Venice Broadwalk Jogger

Bob Cicherillo
Venice Boardwalk Bodybuilder

Ethan S. Smith
Sidney's Buddy

Nelson Franklin
Sidney's Buddy

Ping Wu
Mr. Chu

Jill Bartlett
Woman Leaving Sydney's House

Matt Walsh
Impatient Golfer

Geddy Lee
Geddy Lee - Rush

Alex Lifeson
Alex Lifeson - Rush

Neil Peart
Neil Peart - Rush

Melissa Rauch
Woman Jogger Yelling at Sydney

David Wain
Wedding Photographer

Raquel Bell
Saks Fifth Avenue Saleswoman

Larry Wilmore
Justice Of The Peace

Dennis James Anderson
Hank Mardukas

Craig Wedren
Wedding Band

Damian Kulash
Wedding Band

Timothy Nordwind
Wedding Band

Dan Konopka
Wedding Band

Andy Ross
Wedding Band

David Krumholtz
Sydney's Buddy (uncredited)

Sidow Sobrino
Rush Concert Fan (uncredited)