- Matthew McConaughey
- Moondog
- Snoop Dogg
- Lingerie
- Isla Fisher
- Minnie
- Stefania LaVie Owen
- Heather
- Martin Lawrence
- Captain Wack
- Zac Efron
- Flicker
- Jonah Hill
- Lewis
- Jimmy Buffett
- Jimmy Buffett
- Donovan St V. Williams
- Snoop's Rasta Pilot
- David Bennett
- Homeless Phil
- Clinton Archambault
- Lawyer
- Joshua Rosen
- Reporter
- Tonya Oliver
- Drug Counselor
- Chela Arias
- Cuban Maid
- Ricardo Matallana
- Jose the Pool Boy
- Joshua Ritter
- Groom "Limp Dick" (Heather's Husband)
- Jo Marie Payton
- Judge
- Karla Goodwin
- Maria
- Debra Cohen
- Tourist Mother
- Alan Frankel
- Tourist Father
- A. Ali Flores
- Neck Brace Guy
- Hunter Rearden
- Tourist Kid #1
- Lefty Korine
- Tourist Kid #2
- Barrie Mizerski
- Pulitzer Announcer
- Todd Mitchell
- Lingerie's Yacht Guard #1
- Devon James
- Lingerie's Yacht Guard #2
- John Morris
- Cash Register Guy
- Andrea Bennetti
- Prostitute #1
- Jenny Ariza
- Prostitute #2
- London Seabreeze
- Topless Woman #1
- Dvorah Kramer
- Topless Woman #2
- Arthur Bivens
- Priest
- Sharon Pfeiffer
- Sexy Older Woman
- Sandro Paes
- Tuba Player
- Dustin Greer
- Robber
- Bertie Higgins
- Bertie Higgins
- Daniele Cecere
- Tourist Teenager
- Francis Allen
- Pulitzer Announcer #2
- Charles Ace
- Gala Patron
- Peter Alexander
- Student
- Sipiwe Anderson
- Restaurant patron
- Jerry Ascione
- Homeless Man
- Van Banoovong
- Drug Rehab Patient
- Rosie Bernhard
- Wheelchair Wedding Guest
- Kailyn Blanco
- Tourist Kid
- Corey Booth
- Homeless Man
- Steven Brack
- Drug Counselor
- Danielle Briana
- Pulitzer Prize Guest
- Stephen L. Cohen
- Armed Guard #2
- Trent Conley
- Tourist
- Ellen Marguerite Cullivan
- Funeral / Bar / PulitzerPrizeGuest (uncredited)
- James 'Slim' Cunningham
- Rehab Patient
- Timothy Mark Davis
- Groomsmen
- Ricky Diaz
- Jonathan / Best Man (uncredited)
- Joey DiSomma
- Bar Patron
- Taina Dominguez
- Bridesmaid
- Tracy Echeverri
- Pulitzer Prize Guest
- Safi El Masri
- Party Guest / Beach Lifeguard (uncredited)
- Frenchi Firecracker
- Drug Counselor
- Sheila Friedman
- Pulitzer Prize Guest / Hospital Waiting Room Visitor (uncredited)
- Corinna Giordano
- Tourist Kid
- Rob Goodman
- Homeless Guy 3
- Mike Guzman
- Sleazy Lawyer
- Rae Hartwell
- Houseboat Girl
- JLynne Herrington
- Wedding Guest
- Paul Homza
- Homeless Guy 2
- Grant Koo
- Groom
- Laurel Levey
- Nurse
- Dawn Lyn
- Tourist
- Audrey Lynn
- Dancing Gala Guest
- Cougar MacDowall
- Jake
- Jamil Malik
- Court Bailiff
- Nick Puya
- Jax
- Nadia Quezada
- Stripper
- Ashae Reagan
- Wedding Guest
- Jeff Remas
- Pulitzer Prize Guest
- Jarrett Ricker
- Yacht Club Guy
- Megan Seely
- Waitress
- Nicholas Simmons
- Armed Guard #1
- Erik Stone
- Bouncer
- Marcelle Taha
- Waitress
