Two and a Half Men: Season 4

2006
24 episodes

Change is in the air as Charlie's bachelor lifestyle meets new romantic twists, while Alan deals with ex‑wife drama and Jake continues to steal every scene.

Season 4 of Two and a Half Men premiered on September 18, 2006 and has 24 episodes, from "Working for Caligula" to "Prostitutes and Gelato". The last episode aired on May 14, 2007.

Where to watch Two and a Half Men

In the United States, you can stream Two and a Half Men on Peacock, Philo, YouTube TV and USA Network. You can also buy it on Amazon Video, Apple TV Store, Google Play Movies and Fandango At Home. It is on streaming services in 127 countries.

Where to watch

Episodes

Episode 1Working for CaligulaAired September 18, 2006
Charlie returns to his bachelor lifestyle after Alan moves out of the house. Alan suffers a breakdown after his divorce from Kandi.
- 22m
- Directed by Gary Halvorson
- Written by Lee Aronsohn and Chuck Lorre
Guest stars
- Melanie Lynskey Rose
- April Bowlby Kandi
- Sandra McCoy Tina
- Marisa Tayui Sally
- Mia Kelly Cindy
- Katie Weaver Marie
- John Dewis Man
- Leah Fitzpatrick Woman
Episode 2Who Is This Vod Kanockers?Aired September 25, 2006
Charlie finally tells Alan that he didn't marry Mia because she wanted Alan and Jake to move out of the house, but Alan finds a hole in his logic. Charlie and Alan deal with a noisy neighbor who constantly sings all the time, who happens to be Steven Tyler.
- 22m
- Directed by Gary Halvorson
- Written by Susan Beavers, Chuck Lorre, Lee Aronsohn and Eddie Gorodetsky
Guest stars
- Melanie Lynskey Rose
- Natalie Denise Sperl Janie
- Steven Tyler Steven Tyler
Episode 3The Sea Is a Harsh MistressAired October 2, 2006
Charlie tries to surf to impress Dottie, a beautiful woman he just met, but after he nearly drowns he is convinced that he saw his late father.
- 21m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Eddie Gorodetsky and Mark Roberts
Guest stars
- Melanie Lynskey Rose
- Brian Patrick Wade Sam
- Nectar Rose Dottie
- Robert Clotworthy Gangster #1
- Jim Meskimen Gangster #2
Episode 4A Pot-Smokin' MonkeyAired October 9, 2006
Alan tries to hire his ex-wife's lawyer to help him win custody over the dog he and Kandi shared.
- 21m
- Directed by Gary Halvorson
- Written by Lee Aronsohn, Susan Beavers, Chuck Lorre and Bill Prady
Guest stars
- April Bowlby Kandi
- Michael Patrick McGill Officer Smith
- Christopher Neiman Joel
- Andre Ware Officer Chamberlan
Episode 5A Live Woman of Proven FertilityAired October 16, 2006
Alan is overjoyed by the prospect of Judith remarrying, as he would no longer have to pay alimony. Alan gets Charlie to help him when it looks like the marriage maybe derailed due to Jake's dislike of his mother's fiancé.
- 21m
- Directed by Gary Halvorson
- Written by Lee Aronsohn, Don Foster, Chuck Lorre and Susan Beavers
Guest stars
- Melanie Lynskey Rose
- Iryna Blokhina Woman
- Ryan Stiles Herb
Episode 6Apologies for the FrivolityAired October 23, 2006
Charlie is dating a woman whose personality and life are like his mother's.
- 20m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Mark Roberts and Don Foster
Guest stars
- Melanie Lynskey Rose
- Katherine LaNasa Lydia
- Andy Pessoa Andy
- Brandon Killham Joey
- James Edson Stephan 'Bobby' Wasserstein
Episode 7Repeated Blows to His Unformed HeadAired November 6, 2006
Berta's daughter, Naomi is pregnant and Berta drags Charlie with her when she confronts the baby's father. Alan reveals a secret fetish.
- 21m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Jim Patterson and Eddie Gorodetsky
Guest stars
- Sara Rue Naomi
- Andy Mackenzie Ronald Wiedermeier
- Julianne Grossman Mrs. Wiedermeier
- Treisa Gary Nurse Shelby
- Rebecca Avery Pregnant Woman
Episode 8Release the DogsAired November 13, 2006
Alan suffers from insomnia. He visits his psychiatrist, who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life.
- 22m
- Directed by Gary Halvorson
- Written by Jim Patterson, Lee Aronsohn, Chuck Lorre and Susan Beavers
Guest stars
- Melanie Lynskey Rose
- Kelly King Kelly
- Larry Cedar Policeman #1
- Melanie Abramoff Taylor
- Bruno Amato Officer Roberts
- Stefan Umstead Officer Foster
- John Pirruccello Police Helicopter Pilot
- Shane Woodson Man
Episode 9Corey's Been Dead for an HourAired November 20, 2006
Charlie gets tired of Alan's mooching and reaches the breaking point during the brothers' double date. Jake is left home alone for the first time.
- 21m
- Directed by Gary Halvorson
- Written by Lee Aronsohn, Don Foster, Chuck Lorre and Mark Roberts
Guest stars
- Melanie Lynskey Rose
- Danielle Bisutti Vicki
- Rachel Cannon Nina
- Shon Little Snack Bar Cashier
- Brendan Patrick Connor Middle-Aged Guy
- Daniel Benson Teenage Boy
- Annie Mumolo Teenage Girl #1
- Ashley Edner Teenage Girl #2
Episode 10Kissing Abe LincolnAired November 27, 2006
Worrying Charlie may get rid of one of them, Berta and Lydia fight over him. Meanwhile, Kandi does everything she can to stop Alan from selling their condo.
- 21m
- Directed by Gary Halvorson
- Written by Eddie Gorodetsky, Lee Aronsohn, Chuck Lorre and Mark Roberts
Guest stars
- April Bowlby Kandi
- Katherine LaNasa Lydia
- Carrie Stevens Pam
- Christopher T. Wood Arnold
Episode 11Walnuts and DemerolAired December 11, 2006
Charlie's friends and family put a crimp in his plan for a romantic Christmas Eve date. When Evelyn sees who the date is, she goes to great lengths to force a wedge between them.
- 21m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Jim Patterson and Susan Beavers
Guest stars
- Melanie Lynskey Rose
- April Bowlby Kandi
- Jessica Collins Gloria
- Susan Sullivan Dorothy
- Ryan Stiles Herb
Episode 12Castrating Sheep in MontanaAired January 8, 2007
Berta discovers that Alan has been dating her daughter Naomi.
- 21m
- Directed by James Widdoes
- Written by Chuck Lorre, Lee Aronsohn, Eddie Gorodetsky and Mark Roberts
Guest stars
- Sara Rue Naomi
- Marco Sanchez Hector
Episode 13Don't Worry, Speed RacerAired January 22, 2007
Jake shares that he has heard his mother having sex with her fiancée, Herb; this revelation brings up a repressed memory for Charlie. This leads Charlie to seek help from Rose.
- 21m
- Directed by Gary Halvorson
- Written by Lee Aronsohn, Chuck Lorre, Susan Beavers and Mark Roberts
Guest stars
- Melanie Lynskey Rose
- Sab Shimono Hiroshi
- Ryan Stiles Herb
Episode 14That's Summer Sausage, Not SalamiAired February 5, 2007
Charlie sets Alan up with their new neighbour. But he gets jealous when the two form a bond.
- 22m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Jim Patterson and Susan Beavers
Guest stars
- Brooke Shields Danielle
- Deprise Brescia Vanessa
- Carly Thomas Smith Eva
Episode 15My Damn StalkerAired February 12, 2007
Rose is moving to London, and Charlie is surprised by his reaction to the news. Alan lies to a woman he met online.
- 22m
- Directed by James Widdoes
- Written by Chuck Lorre, Lee Aronsohn, Eddie Gorodetsky and Mark Roberts
Guest stars
- Melanie Lynskey Rose
- Allison Janney Beverly
- Lauren Rose Lewis Shannon
- Rebecca McFarland Leanne
Episode 16Young People Have Phlegm TooAired February 19, 2007
Charlie's young, hot girlfriend takes him to a new club. She invites Alan to meet one of her friends but the men are shocked to learn that they are considered as being "old".
- 21m
- Directed by Andrew D. Weyman
- Written by Eddie Gorodetsky, Lee Aronsohn, Chuck Lorre and Mark Roberts
Guest stars
- Brooke D'Orsay Robin
- Lamont Thompson Bruno
- Morgan Fairchild Donna
- Molly Morgan Megan
- Kris Iyer Dr. Prajneep
Episode 17I Merely Slept with a CommieAired February 26, 2007
After Evelyn tells Alan and Charlie how she feels about there being no mourners at her friend's funeral, the boys share their feelings that this could also be the case at her funeral. Evelyn tries to prove them wrong by introducing them to a couple she help adopt a boy from China. The boys return fire by inviting the young man to a play date with Jake.
- 22m
- Directed by Gary Halvorson
- Written by Don Foster, Chuck Lorre, Lee Aronsohn and Jim Patterson
Guest stars
- Tony Tripoli Philip
- Lee Garlington Peggy
- Wayne Wilderson Roger
- Michael Merton Photographer
- Austin Lee Changpu
Episode 18It Never Rains in HootervilleAired March 19, 2007
Alan tries to bond with Jake when he realizes that his childhood is almost over. Kandi pursues a career in acting.
- 21m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Mark Roberts and Don Foster
Guest stars
- April Bowlby Kandi
- Ben Hermes Detective
Episode 19Smooth as a Ken DollAired April 9, 2007
Charlie takes a liking to Myra, the witty sister of Judith's fiancé, Herb.
- 21m
- Directed by Gary Halvorson
- Written by Chuck Lorre, Lee Aronsohn, Eddie Gorodetsky and Susan Beavers
Guest stars
- Sara Erikson Bethany
- Judy Greer Myra
- Ryan Stiles Herb
Episode 20Aunt Myra Doesn't Pee a LotAired April 16, 2007
Alan looks forward to Judith's wedding, while Charlie and Myra continue their romance.
- 21m
- Directed by Jerry Zaks
- Written by Jim Patterson, Eddie Gorodetsky, Lee Aronsohn and Chuck Lorre
Guest stars
- Judy Greer Myra
- Tammy Lauren Shannon
- Bob Rumnock Minister
- Avner Garbi Tailor
- Ryan Stiles Herb
Episode 21Tucked, Taped and GorgeousAired April 23, 2007
Alan and Charlie re-examine their sexual identities after Alan befriends Greg, a gay man. Meanwhile, Jake has a crush on Greg's daughter.
- 22m
- Directed by Jerry Zaks
- Written by Chuck Lorre, Lee Aronsohn, Mark Roberts and Don Foster
Guest stars
- Kay Panabaker Sophie
- Matt Roth Greg
- Dale Waddington Woman
- Jane Lynch Dr. Linda Freeman
Episode 22Mr. McGlue's FeedbagAired April 30, 2007
Jake gets lucky after Charlie takes him to the racetrack. Meanwhile, Alan has a difficult time at the DMV.
- 22m
- Directed by Jon Cryer
- Written by Chuck Lorre, Lee Aronsohn, Jim Patterson and Don Foster
Guest stars
- Andrea Savage Lena
- Nadine Ellis Jeanie
- Doug Mitchell Jim
- Nancy Linari Woman's Voice
- Joel Murray Petey
Episode 23Anteaters. They're Just Crazy-Lookin'Aired May 7, 2007
Charlie is shocked when the handyman working on his house beats him out for Chloe's affections. Alan has no sympathy for Charlie's distress.
- 21m
- Directed by Lee Aronsohn
- Written by Chuck Lorre, Lee Aronsohn, Jim Patterson and Mark Roberts
Guest stars
- Enrique Iglesias Fernando
- Rachel Cannon Chloe
Episode 24Prostitutes and GelatoAired May 14, 2007
Evelyn's boyfriend, Teddy, invites Alan and Charlie to go with him to Las Vegas on his private jet. The boys confront their individual 'daddy issues'
- 20m
- Directed by Ted Wass
- Written by Eddie Gorodetsky, Lee Aronsohn, Chuck Lorre and Susan Beavers
Guest stars
- Mike Connors Hugo
- Robert Wagner Teddy
- Ian 'Blaze' Kelly Jamal
- Bob Rusch Referee
- Jacqueline Lord Tiffany
- Charity Hodges Amber