How I Met Your Mother’s 10 Most Legendary Guest Stars

Over the course of nine seasons of How I Met Your Mother, there have been a tremendous amount of memorable guest stars. From girlfriends of both Barney and Ted to various friends of the gang, there have been ample opportunities for exciting actors to show up in smaller roles. In the 21st episode of season 9, there was a sequence that showed us where many of the most memorable characters are at in their lives by the end of Ted's story. A lot of familiar faces were shown, but it wasn't nearly enough, as even a full episode running through those guest stars couldn't highlight all the beloved ones that have appeared on the show. With HIMYM nearing its end, it seems unlikely that there's going to be any additional significant guest stars for the show. With that in mind, now seems like as good of a time as any to look at which of these memorable characters left the biggest impact. So without further ado, read on to see our picks for How I Met Your Mother's 10 most legendary guest stars. Bryan Cranston as Hammond Druthers You likely know him from Breaking Bad and Malcolm In The Middle, but Bryan Cranston has had his fair share of guest-starring roles on sitcoms. One of the best though is definitely his role as Ted's former boss Hammond Druthers. Not only is Druthers the worst boss in the world, but he also designs a building that looks more than a little bit like a certain male reproductive organ. After working under Hammond, the roles reverse and Ted becomes the boss. Hammond still acts like a jerk though and Ted is forced to fire him. Unfortunately, Ted first tried to do this on Hammond's birthday. He's unable to go through with it though and waits until Druthers is going through a divorce. Cranston reprised the role in season 9, after the conclusion of Breaking Bad and while it was a short, and rather insignificant appearance, the actor is still one of the show's most legendary guest stars. Laura Prepon as Karen In terms of being a good person, Laura Prepon's Karen is just about the most terrible character that the show has featured. The pretentious Karen has always found a way to bring out the absolute worst in Ted, whether it be in the numerous flashbacks or when they dated again in his 30s. Still, for as terrible as Karen is, Prepon excellent in the role. Someone that despicable has to be fun to play, and it looks like the actress relished every moment of it on screen. Delivering every single one of her condescending line with pleasure, Karen is a longtime fan favorite and one that we'll remember long after the show is off the air. Joe Manganiello as Brad Morris Marshall didn't keep in touch with many of his friends from law school once he graduated, but one who always seemed to be popping up in his life was Brad Morris, played by Joe Manganiello. Brad's earliest moments are some of his best, as he comforts Marshall after Lily leaves him. Brad and Marshall become brunch buddies and it almost seems like Brad is infatuated with his new friend. Manganiello plays the role perfectly, especially when he's being overly bro-y about his sentimentality. Brad shows up many times over the years, but he comes back again for another memorable appearance in the season eight episode, Twelve Horny Women. He's the lawyer fighting Marshall in the Gruber Pharmaceutical case and he uses every ounce of his rippling body to win over the all-women jury. After the trial, Brad realizes the harm he's done and ends up being the one to convince Marshall that he should become a judge. While most know Manganiello from True Blood, HIMYM has provided the capable actor with yet another memorable television role. Bob Barker As Himself How I Met Your Mother has featured a few celebrities playing themselves over the years, but no one was more enjoyable than Bob Barker's cameo that occurred when Barney finally got his shot on The Price Is Right. Barney's motivation for going on the show was the fact that he believed Barker was his dad. This belief stems from his mother giving him a flippant answer about who his father was when he was young. Barney used this belief to get him through some tough times over the years and so when he finally gets the opportunity to appear on the show, he jumps at it. Barney absolutely dominates all the pricing games, and while Barker seems to be a little confused by the way Barney is speaking to him, he plays along and is quite a good sport about the entire situation. It's a great episode, and seeing one of the true game show legends make an appearance made for a truly legendary cameo. Will Forte As Randy Wharmpess The hilarious Will Forte is always enjoyable to watch, but it may be when he plays a lovable loser that he's at his best. First appearing as Barney's coworker, Randy Wharmpess turns out to be the world's worst wingman, even though he's the only one on the blogaspehere who reads what Barney has to write. A major problem standing between their broitude is the fact Randy gets a nosebleed every time he has an erection. He thinks about Robin in the shower, too, but I think the nosebleed thing is a bigger problem. Still, for all his shortcomings, Randy is gung-ho about trying to be a great wingman and Forte great in the role. He takes notes of Barney's moments, tries to use "legendary" properly, but is so afraid of women that he can't even be introduced without running to hide under a booth. Randy comes back in season six as a GNB employee that Marshall is forced to fire. He's completely incompetent, and watching Forte bumble around the office is hilarious. Don't worry though, things end alright for him as his firing allows him to start his own warm piss, I mean, Warmpess brewing company. Jorge Garcia as The Blitz One of my all-time favorite episodes of How I Met Your Mother featured Jorge Garcia as Steve"The Blitz" Henry. The Blitz is a sad guy. He's never been all that close with Ted and Marshall, but they've always gotten along, which means they've hung out on occasion over the years. The problem is, those events have always gotten way better after he left, prompting him to exclaim his trademark, "Aw, man!" Steve wasn't the first Blitz, but ever since he became Blitz in 1997 there seemed to be no end to his misfortune. That changed in season six when he showed up for Thanksgiving and found a way to send his Blitzness onto the rest of the gang. It was passed along to everyone and Steve was back to just being Steve. He couldn't have been happier about it either, until he's ultimately reunited with his fate as the unluckiest man alive. Garcia is great as Blitz, and while he doesn't appear that often, it was a true treat to see him again in season 9. I don't think there's anyone else who can let loose a disappointed, "Aw, man" like Hurley. I mean, Garcia. Britney Spears as Abby Britney Spears wasn't still a huge name by the time she appeared on How I Met Your Mother, but let's be real, she's still Britney Spears. Like Katy Perry's Honey, Spears' Abby is completely naive and a bit trashy (what are you trying to say about pop music Bays and Thomas?). Not only is Abby great in her first appearances as Stella's receptionist, but she comes back later in season three for a totally unexpected appearance as the one who's trying to ruin any chance Barney has at sleeping with another girl. She's not able to hold out for long, and the result is a hilarious scene where she believes that Barney's fake proposal is a real one. I'm not the only one who thinks that Abby was legendary either, as in 2009 Spears was nominated for a well-deserved People's Choice Award as Favorite Scene Stealing Guest Star. Billy Zabka as Himself One of Barney's more amusing character traits is the fact that he always roots for the bad guy in movies. He loved Hans Gruber, pulled for the guy running detention in The Breakfast Club, and even cried when the Terminator's little red eye went out at the end. But the one villain he loved more than any other was the Karate Kid himself, Johnny Lawrence. So when Billy Zabka appeared at Barney's bachelor party, Barney couldn't have been any happier. Zabka's appearance went over so well with fans that they decided to bring him back for all of season 9. He's one of Barney's guests at the wedding and at one point he's even the best man. It turns out that he's not only a sensitive guy who hates to be hated, but he's also a poet beloved by Gary Blauman. Billy Zabka is a multia-layered character, and an excellent addition to How I Met Your Mother. James Van Der Beek As Simon Tremblay Some of the best How I Met Your Mother jokes over the years have been mocking Robin's home country and her past. There have been plenty of jabs at Canada and even more laughs from her prior life as a teen pop sensation. One of the most significant parts of Robin's youth though is her first boyfriend, Simon Tremblay, who is played by James Van Der Beek. When they were young and in love, Simon had a band called The Foreskins. Robin was so head over heels from him that she lugged his equipment around for him after shows. To Robin's dismay, Simon dumped her in favor of Louise Marsh, whose parents had just bought a pool. Years later, Simon comes to visit and he hasn't changed at all. While it's funny to watch Van Der Beek play the young Simon, he's truly great as the manchild Simon, still thinking that his job at the water slide park is more important than anyone else's. He briefly gets back together with Robin, but ultimately he has to let her go again. After all, Louise Marsh's parents did just put in a Jacuzzi. Kyle MacLachlan As The Captain My all-time favorite How I Met Your Mother guest star is Kyle MacLachlan as the boat-loving, self-named Captain. When Ted first has a run-in with Zoey, he finds out that she was married to a much older man. A man who loved only one thing more than he loved her: boats. While Ted and Zoey's relationship fizzled, and the fan-opinion on her is split, there's no one that doesn't love the Captain. First of all, he insists people call him The Captain. No one else decided this; he made the decision about his new nickname for himself. After all, a great man gives himself a nickname. Then there's the fact that he always says "Ahoy," which is just so much better than saying hello. He also runs his house like it's a ship, and is rich enough to get away with it. He's far from Ted's usual crowd, too, and that makes him even more enjoyable to watch. There's almost nothing about the Captain not to love. Sure, he's way over the top, but he's still a hilarious and absolutely unforgettable character. Those are our picks for How I Met Your Mother's 10 most legendary guest stars. Are there any that we missed? Share your picks in the comments section below.