- Larry David
- Nathan / Rolly
- Bill Hader
- Rags
- Philip Baker Hall
- McKenzie
- Jon Hamm
- Will Haney
- Kate Hudson
- Rhonda
- Michael Keaton
- Joe Stumpo
- Danny McBride
- Frank
- Eva Mendes
- Jennifer
- Amy Ryan
- Wendy
- J.B. Smoove
- Jaspar
- Amy Landecker
- Nathan's Wife
- Mary Klug
- Tibby
- Patty Ross
- Gladys
- Marianne Leone
- Joyce
- Mike Cerrone
- Poker Buddy
- Lenny Clarke
- Poker Buddy
- Dorothy Dwyer
- Poker Buddy
- Peter Farrelly
- Poker Buddy
- Jimmy Tingle
- Poker Buddy
- Douglass Bowen Flynn
- Police Officer
- Chris Zito
- Ben (Co-Worker)
- Albert M. Chan
- Electron Motors Co-Worker
- David J. Curtis
- Electron Motors Co-Worker
- Michele Proude
- Electron Motors Co-Worker
- Marilyn Cortez
- Nanny
- Forry Buckingham
- Interviewer
- Ian Cardoni
- Barista
- Daniel Greene
- Coffee Shop Patron
- Langston Kerman
- Coffee Shop Patron
- Steve Conrad
- Flirty Guy at Fair
- Rick Malambri
- Flirty Guy at Fair
- Lars Slind
- Flirty Guy at Fair
- Sean Gildea
- Concertgoer
- Cary 'Big Shug' Guy
- Security Guard
- William Ambrose Kennedy
- Carl
- Alexandria Danielle King
- Waitress
- Georgia Lyman
- Dinner Friend
- Paul Scheer
- Dinner Friend
- Christian Mallen
- Howard at 15
- Brendan Meehan
- Young Howard
- Frank Ridley
- Detective
- Scott Severance
- SUV Driver
- Edward A. Sherman IV
- Construction Worker
- Bill Thorpe
- Construction Worker
- Conan O'Brien
- Conan O'Brien
- Robert Lamm
- Self (Chicago Band Member)
- Lee Loughnane
- Self (Chicago Band Member)
- James Pankow
- Self (Chicago Band Member)
- Walter Parazaider
- Self (Chicago Band Member)
- Tom Granger
- Concert Goer
- Jeffrey Adler
- Fair Goer / Concert Attendee (uncredited)
- Giovanni Alabiso
- Fair Goer
- Kilo Alexander
- (uncredited)
- Stephanie Atkinson
- Surprise Party Guest
- Marshall Berenson
- Andrew Klubach
- Geoffrey Blass
- Concert attendee
- Wolf Blitzer
- Self
- Mark Burzenski
- Construction Worker
- Todd Byron
- Chicago Concert Fan
- Jared Cahill
- Extra
- Dexter the Cat
- Rhonda's Cat
- Chemi Che-Mponda
- Pedestrian
- Alessandro Chicarella
- Construction Worker
- Colleen Connelly
- Concert Attendee
- Max Cross
- Chicago Concert Extra
- John Currie
- Boy on Bus
- Tess Degen
- Chicago Fan
- Don Ditson
- Steve
- Christopher Doig
- Concert attendee
- Steven Dougherty
- Construction Worker
- Timothy DuBois
- Chicago Concert Fan
- Frank Durant
- Driver
- Miranda Evans
- Fair-Goer
- Pamela Figueiredo
- Gorgeous Blonde
- Sarah Fischer
- Pub Patron
- Dave Gabanelli
- Concert attendee
- Mark Garrigus
- Concert Goer
- Amanda Gavin
- Patron
- Austin Giles
- Carnival Patron
- Jonna Gillis
- Concert Goer
- Mickey Gilmore
- Construction Worker
- Curtis Grilli
- The Extremely Hairy Man
- London Hall
- CEO
- Rosemary Howard
- Diner Patron
- Christopher Hyder
- Extra
- Marisa Iacomini
- Ferry Goer
- Frankie Imbergamo
- Pub Patron
- Tom Kenny
- Pedestrian
- Jeffery Kincannon
- Chicago Concert - Jack
- David A. Kirsch
- Construction Worker
- Gwen Kosak
- Fairgoer
- Mike Koutrobis
- Construction Worker
- Renee Lawrie
- Concert Attendee
- Savanah Lee
- Concert Attendee
- John Joseph Lindsey
- Concert Security Guard
- Phyllis Lynn
- Concert Goer
- Conan Marchi
- Chicago Fan
- Tom Mariano
- Security Guard
- Daniel Martignetti
- Cook
- Karen Ann Martino
- Window Shopper
- Robert Masiello
- Picture Car at Marina
- Jamie Mazareas
- Concert Goer
- Christopher Mikael
- Feature Fair / Concert Looker (uncredited)
- Wayne R. Miller
- Construction worker
- David Sean O'Donnell
- Fairgoer / Concertgoer (uncredited)
- Joseph Oliveira
- Restaurant Patron
- Richard Pacheco
- Man at the Bar
- Chris Palermo
- Diner Patron
- Jim Patton
- Diner Customer
- Michael J. Peluso
- Construction Worker
- Jay Peterson
- Security Guard
- Elizabeth Provencher
- Fair Go-er / Concert Attendee (uncredited)
- Suzanne Prunty
- Restaurant Patron
- Jeannine Reardon
- Concert Goer
- John P. Russo
- Concert Attendee
- Matthew Ryan
- Pedestrian
- Megan Sacco
- Chicago Concert
- Liev Schreiber
- Tibor
- David Struffolino
- Concert Attendee
- Ben Tanguay
- Chicago fan
- Carole Taylor
- Fair & Concert Attendee
- J.T. Turner
- Pool Man
- Pamela Valentine
- Fairgoer, Chicago fan
- Maria Vasallo
- Concert patron
- George J. Vezina
- Clamshack customer at counter
- Jan Waldman
- Fair Attendee
- Forrest Weber
- Chicago Fan
- Jamie Christopher White
- Pool Player #1
- Andrew Wynne
- Construction Worker
- William Xifaras
- Diner Patron
