Two and a Half Men debut on CBS in 2003. Starring Charlie Sheen, it quickly became a favorite. The plot, a narcissistic jingle writer living next to the beach with his broke brother and dumb nephew, turned out to be Emmy-worthy. During its reign, it bagged a record of 46 nominations, winning six technical awards. For the first eight seasons, Charlie Sheen bodied his character ‘Charlie’. It is assumed that he perfectly fit the role, as it wasn’t so far from his life as a celebrity. His charming ladies’ man traits, coupled with Berta’s (Conchata Ferrell) no-nonsense persona, Alan’s ( Jon Cryer) rigid beliefs, and Jake’s (Angus Jones) complete lack of basic life skills, made television gold.
The show took a nosedive after the exit of Charlie Sheen and only lasted four more seasons after his departure. Through Charlie’s reign and the last four seasons where he was replaced by Ashton Kutcher, a few celebrities popped in and out. Some stayed a bit longer than others. Let’s see who:
10 Enrique Iglesias
In the fourth season of the show, the King of Latin pop appeared as ‘Fernando’, a handyman. The May 2007 episode was plotted around Charlie’s deck. Fernando was hired to fix the deck. The ladies of the house, especially Charlie’s love interest Chloe (Marin Hinkle) could not help themselves. Eventually, Chloe left and ‘promised’ to see Charlie soon.
9 Bellamy Young
Before she was ‘smelly Mellie’ on Scandal, Bellamy Young, then an upcoming actress, made an appearance on the show. She played ‘Diane’, a money-hungry predator who met Alan at an auto shop. She was drawn to Alan’s Mercedes. Unknown to her, the car was borrowed. Alan let the lie run and drove her to his mum’s Beverly Hills mansion. The night ended fatefully for Alan when he was robbed of a few valuables.
8 Mila Kunis
On the eleventh season of the show, Mila Kunis appeared alongside her husband Ashton Kutcher (Walden Schmidt). In the episode, Vivian was peering through Walden’s doors. He let her in and convinced her to wait until the storm went away. Vivian stayed, and the two bonded over Chinese food. The next morning, Vivian left, although Walden had already pictured a life with her.
7 Tim Conway
Comedian Tim Conway appeared on a single episode during the eleventh season of the show. He was a friend of Marty Pepper (Carl Reiner), a boyfriend of Evelyn Harper (Holland Taylor). When Marty decided to marry Evelyn, Tim appeared at his bachelor party. At the wild bachelor party, Marty, after getting a lap dance, called off the wedding and took the strippers home.
6 Miley Cyrus
Singer Miley Cyrus appeared on Season 10 of Two and a Half Men as ‘Missi’, the girlfriend of Jake Harper. On the two-episode stint, Missi and Jake met right as Jake was about to head off to Military camp. They appeared to get along, but it was apparent that Jake’s infatuation was unrequited. By the end of their time together, Missi had revealed that she was in a relationship. She also convinced Jake to go back to the army.
5 Megan Fox
On the 12th episode of the first season, Megan Fox guest-starred on the show as the teenage daughter of Berta, ‘Prudence.’ Berta was forced to bring her daughter to work. However, the teenage girl was stubborn, and even made advances towards Charlie. Seeing as she was underage, Charlie tried to resist her trap. Despite his philandering ways, he managed to keep it together.
4 Denise Richards
Actress Denise Richards, who once had a real-life relationship with Charlie Sheen appeared on two episodes of the show. She was cast as ‘Lisa’, one of Charlie’s love interests. In her first appearance, Charlie tried to woo Lisa back into his life and invited her to a thanksgiving dinner where everyone was bribed to be nicer to him. When she re-appeared in the second season, the lovebirds had a fling that did not end well.
Way before she was a known singer, Tinashe was cast as ‘Celeste’ on four episodes of Two and a Half Men. Celeste and her father moved to Malibu. She and Jake quickly became friends and began dating. She became more controlling in the relationship, a trait that Jake was irked by. Their relationship ended when she caught Jake cheating.
2 Hillary Duff
In Season 10’s finale, Hillary Duff appeared a ‘Stacey’, a love interest of Walden (Ashton Kutcher). Stacey was an uninterested girlfriend who was constantly on her phone. Things took a different turn When Walden, after moments of being ignored, found himself attracted to Stacey’s grandmother, Linda ( Marilu Henner). Linda first turned him down, and later gave in when he became more persistent. Stacey approved of the relationship, calling Walden the ‘old guy.’
1 Michael Clarke
Actor Michael Clarke, who passed away in 2012, made a cameo as ‘Jerome’. When Jerome moved to Malibu with his daughter Celeste (Tinashe Kachingwe), his strong physique intimidated his neighbors. He was protective of Celeste and was upset when she didn’t come home early after a date with Jake. In the second episode, he was warmer and even shared a drink with Alan, Herb (Ryan Stiles), and Gordon (J. D. Walsh)
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About The Author
(16 Articles Published)
Nataly Owala is a seasoned writer based in Nairobi, Kenya. Her writing career debuted on Magazine Reel, an online campus news site. She’s written articles, newsletters, PR content and has managed to co-author and edit a few books while at it. Writing, to her, is a passion that has taken a life of its own.
When she’s not posting on TheThings, she is buried in a good memoir, over a hot cup of coffee.
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