Two and a Half Men (2003-2015) has been a hit sitcom for a whopping 10 seasons. Of course, with 262 episodes, you can probably imagine that this cast was supplemented by many, many famous celebrity guest stars. While there are almost too many good ones to create such a short list, we broke it down to 10 guest stars that you might have forgot even appeared on this famous show. So here are our favorite 10, ranked from earliest appearance to the newest season.
Megan Fox, as “Prudence”
The young Megan Fox played Berta’s granddaughter, Prudence in the first season of the show, appearing in the episode “Camel Filters and Pheromones”. While Megan has always been beautiful and brilliant, of course, it becomes pretty hard for the boys to keep their eyes off of Berta’s young granddaughter. Even more so, they’re pretty terrified that Berta might kill them if they don’t. Yet honestly, we’re not even blaming them. Megan is always stunning, and boy she killed this guest appearance.
Allison Janney, as “Beverly”
In season 4, the episode “My Damn Stalker”, this hilarious woman plays Alan’s tall and intelligent blind-date. While Allison is known for her comedic role on the new sitcom, Mom, she’s not new to the big screen. Allison usually finds her place in Hollywood movies, but we weren’t complaining about her taking this sitcom role. In fact, this character was pretty funny, and we were rooting for her and Alan.
Allison always makes our belly hurt from laughing, but we also loved this more humble role for her.
Enrique Iglesias, as “Fernando the Handyman”
In season 4, in the episode “Anteaters, They’re Just Crazy-Lookin’”, this handsome and famous singer blew us all away when we turned on our favorite sitcom. Honestly, this is probably our favorite guest appearance, as his episode had us all laughing the entire time. This humble and, well, secret-womanizer handyman had us rooting for him the entire time, and he fooled us as much as he fooled Charlie. Enrique slammed this role, and we even get to hear his angelic voice. We’re not exactly blaming every single woman in this episode for falling all over him. Like, wouldn’t you?
Jason Alexander, as “Dr. Goodman”
In the 200th episode (Season 9) of this hit sitcom, this Seinfeld alum appeared in the episode “The Straw in My Donut Hole” to play the strange (and kind of depressing) doctor.
Jason Alexander is definitely not new to us, and if you watch sitcoms, you’re definitely familiar with this hilarious man. With six Emmy nominations and three Golden Globe nominations under his belt, it’s pretty clear why we always find him brilliant. We love you George. Uh, we mean, Jason.
Miley Cyrus, as “Missi”
In two episodes of season 10 (“You Do Know What the Lollipop is For” and “Avoid the Chinese Mustard”), Missi plays the ex-girlfriend of Jake, appearing after Jake returns home on leave. While Miley is more than accustomed to the television screen, she is always catching our attention. Missi is sporadic, loud, and, well, never stops talking. But honestly, we’re listening to every word she’s saying, because this pop-singer actress absolutely stole the show with this hilarious character.
Hilary Duff, as “Stacey”
In the season 10 finale, “Cows, Prepare to Be Tipped”, this Family star returned to the television screen to play Walden’s girlfriend. While Hilary hasn’t exactly made a splash in Hollywood since her Family channel days, we were more than happy to see her return to our television screens. Stacey is pretty drunk for the majority of this episode, and we’re applauding Hilary’s dedication to this role.
We miss you, girl.
Heather Locklear, as “Laura Lang”
This soap opera star appeared in the first season of this show, and plays Alan’s vengeful attorney. Of course, this woman sinks her claws into Charlie, putting Alan in a very difficult situation when his brother breaks her heart. This episode is classic Charlie, and classic Alan getting the worst of his mess. We definitely don’t want to mess with Laura, but unfortunately, Charlie already did. Also, we’re marking this as the birth of Judith totally killing Alan in the divorce.
Denise Richards, as “Lisa”
Appearing in the first and second season, Denise plays Charlie’s old flame. Ironically, this actress was actually married to Charlie Sheen (although they got divorced over the show’s run). However, Lisa clearly has Charlie’s heart, and this is probably the first time we see the sensitive side of this womanizer. Although Denise is more well-known for her modeling career, we still love to see her on our television screen.
We loved Lisa’s humble and fiery nature, and we were kind of sad to see her go.
Mila Kunis, as “Vivian”
Like Denise, this stunning actress was also married to the leading man, except this time it’s Ashton Kutcher. In season 10, during the episode “Lan Mao Shi Zai Wuding Shang”, Vivian appears, quite literally, on Walden’s deck. Walden becomes infatuated, but Vivian’s adventurous personality cannot be tamed by him. Walden gets kicked in the balls twice this episode, and loses his girlfriend and Vivian. Yikes, but you know, at least Ashton has this brilliant woman in real life, right?
Judy Greer, as “Myra Melnick” and “Bridget Schmidt”
This brilliant actress actually blesses our screens in two different seasons. First, she appears in season 4 as Herb’s sister. Then later, she reappears in the later seasons (9 & 10) as Walden’s crazy ex-wife. Both times, and playing two very different characters, Judy made us laugh and cringe with her brilliant acting expertise. Judy is known for her sitcom cameos, and quite frankly, she always plays someone pretty strange, but we’re loving it all the same.
