The BEST episodes of Two and a Half Men season 5

Every episode of Two and a Half Men season 5, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Two and a Half Men season 5!

Charlie is a well-to-do bachelor with a house at the beach, a Jaguar in the front, and an easy way with women. His casual Malibu lifestyle is interrupted when his tightly wound brother Alan, who's facing a divorce, and his son Jake, come to live with him. Together, these two and a half men confront the challenges of growing up; finally. Complicating matters are the brothers' self-obsessed, controlling mother, Evelyn, Alan's estranged wife, Judith and Charlie's crazy neighbor Rose, who wants to be a part of his life and is willing to do anything to be around. After the death of his brother, Alan Harper meets and befriends a lonely young man named Walden Schmidt who turns out to be a billionaire. Unable to afford his brother's home, Alan sells Walden the house, and as a way of showing his gratitude, Walden allows Alan and his son Jake to move in with him.

Last Updated: 11/7/2024Network: CBSStatus: Ended
Share:
Fish in a Drawer
star
7.73
2506 votes

#1 - Fish in a Drawer

Season 5 - Episode 17 - Aired 5/5/2008

CSI's investigate a death at Charlie's house.

Directors: Jeff Melman
Watch Now:Amazon
Kinda Like Necrophilia
star
7.64
2694 votes

#2 - Kinda Like Necrophilia

Season 5 - Episode 10 - Aired 11/26/2007

Alan finds out that Charlie stole his girlfriend and works on a plan to get back at Charlie, even though this happened when they were in high school.

Directors: Ted Wass
Watch Now:Amazon
Tight's Good
star
7.64
2538 votes

#3 - Tight's Good

Season 5 - Episode 9 - Aired 11/19/2007

Charlie fights his attraction for Teddy's daughter.

Directors: Jean Sagal
Watch Now:Amazon
Media Room Slash Dungeon
star
7.59
2797 votes

#4 - Media Room Slash Dungeon

Season 5 - Episode 2 - Aired 10/1/2007

Charlie acts strange after spending an evening with his mother, and a woman Alan slept with behaves oddly the next morning.

Directors: Ted Wass
Putting Swim Fins on a Cat
star
7.58
2616 votes

#5 - Putting Swim Fins on a Cat

Season 5 - Episode 5 - Aired 10/23/2007

Charlie has to come up with ways to keep his girlfriend's 4-year-old amused; Alan becomes a test subject.

Directors: James Widdoes
The Soil Is Moist
star
7.55
2628 votes

#6 - The Soil Is Moist

Season 5 - Episode 13 - Aired 3/31/2008

Alan finds out some surprising information about Judith's sex life when he decides to go on a date with one of her friends.

Directors: James Widdoes
Waiting for the Right Snapper
star
7.55
2611 votes

#7 - Waiting for the Right Snapper

Season 5 - Episode 19 - Aired 5/19/2008

When Charlie meets Angie's soon to be daughter-in-law, he realizes it's not for the first time.

Directors: Jeff Melman
Look At Me, Mommy, I'm Pretty
star
7.55
2629 votes

#8 - Look At Me, Mommy, I'm Pretty

Season 5 - Episode 16 - Aired 4/28/2008

Alan makes wedding plans for Evelyn and Teddy, while Charlie figures out how to get more acquainted with his future step-sister.

Directors: Joel Zwick
Large Birds, Spiders and Mom
star
7.55
3245 votes

#9 - Large Birds, Spiders and Mom

Season 5 - Episode 1 - Aired 9/24/2007

Jake is getting ready to start a new school as he graduates to Junior High. Alan and Charlie take him school shopping and find themselves in trouble.

Directors: Ted Wass
City of Great Racks
star
7.54
2743 votes

#10 - City of Great Racks

Season 5 - Episode 4 - Aired 10/15/2007

Charlie and Linda get closer to consummating their relationship, but Charlie has trouble focusing when he begins to see Rose's face everywhere he turns.

Directors: James Widdoes
Winky-Dink Time
star
7.54
2566 votes

#11 - Winky-Dink Time

Season 5 - Episode 14 - Aired 4/14/2008

Charlie double-dates with Jake and fixes Alan up with a hooker.

Directors: James Widdoes
Is There a Mrs. Waffles?
star
7.51
2705 votes

#12 - Is There a Mrs. Waffles?

Season 5 - Episode 8 - Aired 11/12/2007

Charlie writes a children’s song and finds success as Charlie Waffles. The children love him and the mothers seem to as well. Charlie's new found fame irritates Alan.

Directors: Ted Wass
Dum Diddy Dum Diddy Doo
star
7.47
2658 votes

#13 - Dum Diddy Dum Diddy Doo

Season 5 - Episode 3 - Aired 10/8/2007

Alan convinces Charlie that he needs to date more respectable women and sets him up with a judge. The two double date and their waitress happens to be one of Alan's ex-girlfriends. Charlie's date backfires the following morning, when he ends up in court in front of the judge.

Directors: Ted Wass
Help Daddy Find His Toenail
star
7.46
2711 votes

#14 - Help Daddy Find His Toenail

Season 5 - Episode 6 - Aired 10/30/2007

Charlie's girlfriend is embrassed to go out in public with him. Meanwhile, Jake sneaks out to attend a concert.

Directors: James Widdoes
Rough Night In Hump Junction
star
7.46
2498 votes

#15 - Rough Night In Hump Junction

Season 5 - Episode 15 - Aired 4/21/2008

Alan feels Charlie is unable to control his womanizing ways.

Directors: James Widdoes
The Leather Gear Is in the Guest Room
star
7.45
2529 votes

#16 - The Leather Gear Is in the Guest Room

Season 5 - Episode 7 - Aired 11/5/2007

After Alan and Charlie have a fight about Alan's role in the house. Alan packs Jake up and moves in with his mother.

Directors: Ted Wass
A Little Clammy and None Too Fresh
star
7.45
2501 votes

#17 - A Little Clammy and None Too Fresh

Season 5 - Episode 12 - Aired 3/24/2008

Rose returns from England, and plays nurse rather oddly for an ill Charlie.

Directors: James Widdoes
Meander to Your Dander
star
7.41
2469 votes

#18 - Meander to Your Dander

Season 5 - Episode 11 - Aired 3/17/2008

When Alan finds himself wanting to break up with a woman, Charlie offers his expertise.

Directors: James Widdoes
If My Hole Could Talk
star
7.29
2614 votes

#19 - If My Hole Could Talk

Season 5 - Episode 18 - Aired 5/12/2008

Charlie's attracted to an older self-help author. Alan and Jake clash over a project for school.

Directors: Jon Cryer