Cool Guest Stars Who Played Themselves on “Two and a Half Men”

Two and a Half Men saw some really cool and famous guest stars making their way in and out of the show’s episodes across the seasons. While most of them played characters that suited their personas best, at times even making their way out of their comfort zones and playing completely different characters, there were a few celebrities who did not play according to the script but instead made the script work in line with their personalities! These were the guest stars who played themselves over the many seasons of the show and are still remembered for their appearances. From Steven Tyler to Michael Bolton representing the community of crooners to Sean Penn and John Stamos representing the acting community, they’re all in here!

Eddie Van Halen

Many of his diehard fans believed that Eddie Van Halen‘s appearance on Two and a Half Men brought down his popularity quotient a notch or two but hey, we are certainly not complaining! Any celebrity walking into the show was a pleasant surprise for fans of the show as well as the celebrity and to see Eddie on screen is always a treat, even when he’s walking out of a bathroom with his guitar in tow! Eddie’s appearance has certainly proved to be even more memorable since we recently lost him. A songwriter and musician of repute, and someone who even has his name in the Guinness Book of World Records, there’s no denying the immense popularity of the American legend. So this cameo appearance of him on the show was definitely a wholesome treat for fans of the show as well as the musician. RIP rockstar.

Elvis Costello

A pioneer of the new wave and punk revolution, and certainly a celebrity who could easily have been a part of Charlie Harper’s circle had Charlie Sheen‘s character been a real one, Elvis Costello‘s appearance on the show may have been a part of a crowd of celebrities — some of them you will find higher up this list — but as always, it certainly stood out. With 31 albums to his name and a fan following that is easily way better than any jingle writer would have, we guess it was Charlie’s wayward ways, gambling ways, and a liking for all things good that must have landed him with the list of friends he often showed off on Two and a Half Men. Well, as long we a celebrity or two kept popping by now and then, were sure weren’t complaining! Elvis appeared on the very first episode of the second season of the show, as part of the cigar-smoking and whisky-sipping support group that Charlie had over at his place. Hilariously copying ideas for his songs from Sean Penn’s confessions, Elvis sure left quite an impression as an actor too!

Lynda Carter

When the Wonder Woman of the past pops into a show and stays on for quite a bit, you know the show’s a hit! And that’s exactly what went down when the original Lynda Carter made her way into the show in Season 11. Although this one was past the Charlie Sheen era — we sure would have loved seeing how Charlie Harper would have reacted to this hot celebrity — it did make an impression on the audience. And when Charlie’s on-screen daughter Jenny hooks up with Lynda, one might even say that she was simply fulfilling what would have easily been her father’s wish! Although Jenny herself did not last for more than a season, we did see quite a bit of good ole Charlie’s charm at play in helping her get her some action all along! It certainly was a twist one wouldn’t have expected from Lynda Carter, which made her appearance on the show all the more endearing.

Harry Dean Stanton

An actor, a singer, and a musician par excellence seeing Harry Dean Stanton as a part of Charlie Harper’s rocking support group proved to be quite a surprise for fans. And we loved it! A career that had spanned a whopping six decades and more had made Harry’s name synonymous with everything that’s cool and rocking, and seeing the senior actor making his way into the show did inject us all with heavy doses of nostalgia. Harry’s appearance on Two and a Half Men was also one of his last appearances on screen. The ever-famous and well-loved celebrity passed away on September 15, 2017, but his appearance on the show sure makes for yet another good memory.

Christian Slater

How many of you would have loved to see Christian Slater take over the role of Charlie Harper from Charlie Sheen? Well, if any of you out there dreamed of it at some point, your dream almost came true in the final episode of the series! Dressed in exactly the same clothes as Charlie — the storyline went that they were actually the elder Harper brother’s clothes — Christian finds himself at the station explaining to none other than Arnold Schwarzenegger that he wasn’t the guy the cops were looking for. Found “in a trashed hotel room with a hooker in the closet” Christian finds himself explaining in vain that it wasn’t him that was Charlie Harper. Well, there really wasn’t anyone who could have taken Charlie Sheen’s place in the series but looking at Christian in Charlie’s clothes, something tells us that if it had really come down to it, the Mr. Robot star would have been a perfect fit!

Chuck Lorre

Chuck Lorre may have been the creator of a long lineup of shows but Two and a Half Men is clearly right up there on the list of his best works. And Chuck knows it! As the creator and producer of the show that won millions of hearts, Chuck did go through a lot of ups and downs in his relationship with Charlie Sheen as the main protagonist of the show, and many of these stories even made headlines. But that didn’t stop Chuck from paying homage to all that Charlie brought to the show — many fans even blamed Chuck’s decision of letting go of Charlie for the dismal run that the show had after his exit. In the finale of the series, Chuck had a piano drop from the sky on a character that was meant to be Charlie Harper ringing the doorbell of his Malibu beach house but before viewers could begin ranting at Chuck for doing this, you see yet another piano drop on the creator of the show himself. Oh, we only wish things could have been better between the two. Maybe, just maybe, we would’ve seen a lot more seasons of the show that was Two and a Half Men!

Steven Tyler

Steven Tyler‘s mention has been a constant on the show ever since Berta quit her job after Alan and Jake move into Charlie’s Malibu house. Tired of Alan’s bickering, Berta calls it a day, and after Charlie drives Alan mad, the latter decides to go on and meet Berta to try and get her back. An ever-helpful and always int he know Rose tips off Alan that Berta works at the Aerosmith star’s house. This particular episode only had Steven’s enigmatic voice as he opens the door to the laundry room of his home to witness Alan and Berta in what he described as doing one another. A few more mentions across a few more episodes and soon enough, it was finally time for us to witness Steven on screen! And how! Giving Charlie a cool beating and leaving him with a broken nose, among other things, Steven sure lives up to his macho image, even delivering a cool line, “I’m still picking pieces of your ass out of my boot…”! But what took the cake was Alan confessing how he had lost his virginity to Steven, and of course, he meant to one of Steven’s songs but the rockstar coolly replies, “Well you know what, there’s a lot of the 70s I just don’t remember!” Well, we’ll always remember you popping by on Two and a Half Men Steven, and it sure was a cool gig we’ll always be thankful for!

John Stamos

John Stamos is probably one of the most loved TV personalities of all time, so it was indeed a surprise to see him play himself in the series. If you’ve noticed, John makes an appearance in two seasons, the ninth and the twelfth. The first time around, he’s one of the prospective buyers of Charlie beachfront property and walks out as quickly as walks in, speaking of a rather “bad memory” he had of the place with Charlie. And as we all know, the property was finally bought by Walden Schmidt. John comes by again to the series in season 12 and is part of the finale that had quite a string of celebrities making their way into the series as an ode to all the entertainment it provided through the years.

Michael Bolton

When you can afford to hire none other than Michael Bolton to croon on your behalf during a romantic date, you know you’ve arrived! And that’s exactly what Walden Schmidt manages to do when he hires the talented and sexy Michael to sing on his date. Shown as someone Walden regularly hires to serenade the women he is really crazy about, Michael’s appearance on the show sure proved to be a surprise that was welcomed by Bolton fans and Two and a Half Men fans alike and went on to show just how popular the singer, songwriter, and musician will always be! Of course, the appearance just wouldn’t have been complete without us listening to that beautiful voice and thankfully, Michael does treat us to a few lines! Michael has to his name quite a few cameo appearances across films and television and we sure are glad he chose to grace one of our favorite shows too!

Sean Penn

Yet another member of Charlie’s famous support group that everyone wished they were a part of, Sean Penn sure took the limelight away from just about everyone in the room with his intense portrayal of a man fighting the usual middle-aged challenges in the first episode of the second season of the show. What has us in splits is how he goes after Elvis Costello for trying to note down ideas for his songs. Or making it clear to Charlie that he was the only one in the group not to acknowledge it as a support group! Well, Sean Penn is welcome to grace the screen even if he chooses not to deliver lines so we are just happy we got to see the Academy Award winner in one of our favorite shows, and as himself too!

Hey, Do Let Us Know if We Missed Out On Any Good Ones!

There were only so many celebrities who made an appearance on the show and played themselves and we’re pretty sure we’ve got most of the list covered here. Even so, if you think we should definitely mention another, all you have to do is let us know in the comments section below and we’ll be happy to oblige. Oh, and considering how popular Two and a Half Men has been, you can also let us know if you want us to cover some more stories related to the show. We’re sure we’ll have a blast researching and writing them out for you!

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