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Top 10 Best How I Met Your Mother Guest Stars

VO: Rebecca Brayton WRITTEN BY: Savannah Sher

Over its nine-season run, Ted and the gang had encountered many a talented actor. For this list, we’re counting down our favorite guest performances from this hit sitcom. We’ll be excluding anyone who appeared in more than four episodes. Our list includes Katy Perry, Rachel Bilson, Jennifer Lopez, James Van Der Beek and more! Join MsMojo as we count down our picks for the Top 10 How I Met Your Mother Guest Stars.

Check out the voting page for this list and add your picks: https://www.WatchMojo.comsuggest/%20Top%20ten%20how%20i%20met%20your%20mother%20guest%20stars Special thanks to our users ulllaaaklara, LOATC and Anita Hulda for suggesting this idea!


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Script written by Savannah Sher

Top 10 Best How I Met Your Mother Guest Stars

Over its nine-season run, Ted and the gang had encountered many a talented actor. Welcome to MsMojo, and today we’ll be counting down our picks for the Top 10 How I Met Your Mother Guest Stars.

For this list, we’re counting down our favorite guest performances from this hit sitcom. We’ll be excluding anyone who appeared in more than four episodes.

#10: Rachel Bilson

Before we learned the identity of the titular “mother” near the end of the show’s run, the creators gave fans plenty of red herrings to throw them off the scent. Rachel Bilson played one of these decoy potential mothers; a woman named Cindy who Ted met while working as a professor. As it turns out, they weren’t exactly a great match. However, Cindy’s roommate piqued Ted’s interest the more he learned about her, though she never appeared on screen. That roommate turned out to be Ted’s future wife, so Cindy’s role would be much more important than it initially seemed.

#9: Laura Prepon

In one of the funniest and most out of character guest spots on the show, Laura Prepon appeared several times to play Ted’s high school and college girlfriend, Karen. Lily and Marshall hate Karen, and it’s easy to see why. She’s snobby, she’s self-centered, and ultimately she treats Ted like total crap. Considering Prepon is perhaps best known for her role as the laid-back Donna on “That 70’s Show”, the contrast between the two characters is all the more satisfying for viewers.

#8: Katie Holmes

In an early episode of “How I Met Your Mother”, we see a flashback to a Halloween party from several years earlier, where Ted meets a girl in what he deems a “slutty pumpkin” costume and quickly falls for her. He loses her number though, and every Halloween since has waited for her to reappear. We finally get to meet this enigmatic woman many seasons later, when Hollywood staple Katie Holmes makes an appearance to play the character, whose real name is Naomi. The surprise of seeing such a recognizable face in the role was a pleasant one! Sadly, their relationship doesn’t go as well as Ted had long hoped it would.

#7: Enrique Iglesias

After Ted and Robin break up at the end of the second season, she decides she needs to get away from the city and takes a vacation to Argentina. When she returns, however, she’s not alone. She brings Gael with her; her new boyfriend who the gang deems her “rebound guy”. Though initially skeptical of him, even Marshall isn’t immune to his charms – while his looks and massage skills have the girls swooning. However, his and Robin’s differences in personality eventually come to a head, leading to their breakup. That said, we won’t be forgetting Iglesias’ performance anytime soon!

#6: Jennifer Lopez

When J. Lo came to the set of “How I Met Your Mother”, it seemed like Barney had finally met his match. Lopez plays Anita Appleby, a woman Robin interviews about her book, "Of Course You're Still Single, Take a Look at Yourself You Dumb Slut". Barney is intrigued by this relationship expert and her techniques, and vows to woo her despite her strict dating rules. Lopez is hilarious in the role, which is reminiscent of some of the excellent romcom work she did in the early 2000s.

#5: James Van Der Beek

Katie Holmes’ appearance was certainly memorable, but she wasn’t the first Capeside resident to interact with the gang. James Van Der Beek made his first appearance in the show’s third season, where he played Robin’s ex-boyfriend from back when she was an up-and-coming teen pop star. And anytime you get a flashback to Robin’s life in Canada, you know it’s going to be good. His character, Simon, is visiting New York, and Robin is charmed by him despite the rest of the gang not quite understanding his appeal. Van Der Beek shines in the role, playing the inexplicably confident burnout to perfection.

#4: Katy Perry

When mega pop star Katy Perry appears on the show, she plays a character referred to as “Honey”, Of course, that’s not actually her real name. But given that the gang only remembers her for her gullibility and naivety, which prompts them to often say to her, “Oh Honey...”, it’s the only name they can remember. She’s Zoey’s cousin, and her character becomes the object of affection for both Barney and Ted. Though she’s only in one episode, Perry's performance is so charming that it’s nonetheless memorable. While she isn’t exactly known for her acting, she impressed viewers with how convincingly she played the character.

#3: Will Forte

Comedy veteran Will Forte appeared on “How I Met Your Mother” to play Randy, a coworker of Barney’s from Goliath National Bank. His role is one of the most hilarious – and cringeworthy – on our list, as Randy has some confidence problems when it comes to communicating with women. Barney tries to take him on as his new wingman, but unfortunately Randy isn’t quite up to the task. That said, Barney does manage to help him overcome his fear of speaking to women, so all’s well that ends well!

#2: Bryan Cranston

Though he may have gotten his start in comedy, Bryan Cranston has made a name for himself with more serious roles in recent years. This makes his stint as Hammond Druthers all the more amusing. He plays Ted’s boss at his architecture firm, and his personality is both frightening and absolutely ridiculous. Lily decides to impart some of her Aldrin Justice on him, which doesn’t play out exactly as she imagined. Eventually, Druthers shows his more sensitive side when Ted takes him in during a rough patch in his life. Sadly, their newfound friendship didn’t last.
Before we unveil our top pick, here are a few honorable mentions.

Lucy Hale

Mandy Moore

Nicole Scherzinger

#1: Britney Spears

The most memorable guest performance on this show has to go to Britney Spears, who made two appearances on the show’s third season. Spears’ acting may not win any awards, but the character she plays is so funny that no one could possibly mind. Abby is a receptionist at Stella’s office, who develops a massive crush on Ted. Of course, Barney inevitably takes advantage of her vulnerability. In the end, however, the two team up in an attempt to get back at Ted in the most hilarious way possible.


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