Top 20 Best How I Met Your Mother Guest Stars
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Top 20 Best How I Met Your Mother Guest Stars

VOICE OVER: Rebecca Brayton WRITTEN BY: Kim Mabee
These "How I Met Your Mother" guest stars stole the show. Our countdown includes James Van Der Beek, Ralph Macchio, Carrie Underwood, and more!
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Top 20 How I Met Your Mother Guest Stars


Welcome to MsMojo, and today we’re counting down our picks for the Top 20 best How I Met Your Mother Guest Stars.

For this list, we’ll be looking at characters that we saw in only one or a few episodes throughout the sitcom whose appearances added much to the episodes in which they were featured and were memorable for the audience.

If we missed one of your favorite celebrity appearances on the show, let us know in the comments.

#20: Carrie Underwood
“Hooked”


We aren’t used to seeing this country singer on our screens when she’s not flaunting her vocal chops, but she was a welcome addition to How I Met Your Mother when she played Tiffany in season 5. She has Ted on her “hook,” as he’s the guy she keeps around in case she needs someone or a relationship doesn’t work out - and because he makes her feel good. This causes Ted to realize that he has a girl on his hook, and Underwood’s Tiffany is on someone else’s hook. So Ted decides to break the chain by ending things with Tiffany, which means her tenure on the show is just a short, one-episode arc. Regardless, this pharmaceutical sales rep had us hooked throughout her appearance.

#19: Ashley Benson
“Ring Up!”


In an attempt to feel younger as he gets back on the dating scene, Ted starts seeing the barely legal Carly. Ted meets her when she sells him a leather cuff and they go on some whirlwind dates before he realizes they have nothing in common. Between her tech savvy vocabulary and obsession with Ted’s age, they find it hard to make a real connection, especially when Ted finds out that Carly is Barney’s half-sister. We were hoping to see her at Barney’s wedding, having a mini Pretty Little Liars reunion with Lucy Hale, who plays Robin’s sister. But, we’re still happy we got to see her on the show during her brief relationship with the lovelorn protagonist.

#18: Danica McKellar
“The Pineapple Incident” & “Third Wheel”


Making two memorable appearances on the show, Danica McKellar plays Trudy, who we see first in season 1. She plays the mystery woman who Ted finds in his bed alongside a pineapple in one of the show’s most watched episodes. Later on in season 3, she makes her second and final appearance on the sitcom alongside Busy Philipps, as one third of the tricycle that may or may not have earned Ted “the belt.” Trudy is even brought up later on in the show, as Lily and Marshall decide whether or not to call her when they forget to set up a date for Ted. Her character is mentioned one last time when Ted is calling everyone he knows in hopes someone will go to a Weird Al concert with him, proving that her appearance really resonated with the gang and viewers alike.

#17: Tim Gunn
Various


Playing a fictional version of himself, Tim Gunn makes several appearances throughout the show’s run as Barney's tailor. We first see him in the show’s 100th episode that features other notable guest stars, like Rachel Bilson and Stacy Keibler, as he helps Barney after a suit mishap. We wouldn’t see Gunn again until the final season, as he joins the gang at Barney and Robin’s wedding, where he makes Barney a special wedding suit for the occasion. We weren’t the only ones who loved it when Tim Gunn popped by the set of How I Met Your Mother, as the cast and crew reportedly asked him for more autographs than any other guest star that appeared on the series.

#16: Jane Seymour
“Aldrin Justice”


Former bond girl Jane Seymour guest starred on How I Met Your Mother in season 2 as Marshall’s constitutional law professor. Marshall tells Barney that she recently went through a divorce and he thinks she is taking it out on her students by grading them poorly. Barney decides to pursue her, but his attempts only result in her grading her students, and Barney, more harshly. Her appearance as Columbia professor’s resident “cougar” was a memorable and welcome surprise as a character who keeps Barney from completing one of his many challenges. In the end, she leaves her mark by giving Marshall a good enough grade and Barney a dislocated hip.

#15: Mike Tyson
“Bad Crazy”


As Robin struggles to connect with Marvin in Lily’s absence, refusing to hold him even when he starts to cry, she calls on help from a stranger to help calm him down. As Robin retells the story to Lily much later on, it takes her nearly 20 years to finally reveal the truth about what happened that day. The story had always been that an older woman helped her soothe Marvin, but in truth it was Mike Tyson, who Lily reveals is a senator in the year 2030 - hey, crazier things have happened. We love seeing guest star appearances on How I Met Your Mother that feature people playing themselves, and Mike Tyson’s surprise reveal was as shocking for Lily as it was for the audience.

#14: Lin-Manuel Miranda
“Bedtime Stories”


While the most memorable aspect of this episode may be that the entirety of the script rhymes, it should be remembered for Lin Manuel Miranda’s appearance as Gus. As Marshall tries to get Marvin to sleep on the bus to Farhampton, Miranda’s character sits across the aisle from him and helps him to come up with some rhymes as Marshall tells his son stories about the gang. Because of this, we get to see the Hamilton writer and star bust out his rapping chops a few years before the famous Broadway play he's known for hit the stage. While his appearance may have been brief, it is fun to look back on now, knowing how successful Miranda’s career was about to become.

#13: Heidi Klum
“The Yips”


When Barney encounters Rhonda, the woman that he lost his virginity to, again, he is dismayed to find out that he wasn’t as big of a stud in the bedroom as he thought. His confidence is shaken and the smooth-talking ladies man comes down with a case of the yips. This couldn’t have happened at a worse time, as he attends a Victoria’s Secret afterparty where he trips over his words while trying to chat with none other than Heidi Klum. Many other real-life supermodels make appearances in this episode, but Heidi Klum is the most noteworthy, and the one who Barney had dibs on. In the end, she finds a solution for Barney’s problem - he needs to go and prove to Rhonda that he can really rock her world.

#12: Ralph Macchio
“The Bro Mitzvah”


On what is seemingly the worst night of Barney’s life, the gang tries to give him a memorable bachelor party. Barney had previously given them a checklist of things to include, with one item being an appearance by the Karate Kid. So when the karate kid himself, Ralph Macchio, shows up, Lily is just as excited as all of us to see him. Barney doesn’t quite feel the same way, despite the fact that he and Macchio appear to have a lot in common. Barney had always considered William Zabka, the antagonist of the film, to be the true Karate Kid, and while his reveal in this episode is also unforgettable, Ralph Macchio is the real Karate Kid everyone was hoping to see.

#11: Lucy Hale
“First Time in New York” & “Vesuvius”


When Robin’s little sister, Katie, comes to visit in season 2, we see a young Lucy Hale who was not as notable of a guest star as she was by the time we see her again in the final season. In between those seasons, the actress’ career had completely taken off, and this left audiences wondering if we’d see another appearance from her before the end of the show. On the morning of Robin’s wedding, Katie is revealed when she removes her goalie mask, playing hockey with Robin as her older sister prepares for her big day. Both of Hale’s appearances are equally memorable, and we loved watching the Scherbatsky sisters bond over hockey and boys throughout the episodes Hale appeared in.

#10: Rachel Bilson
“Girls vs. Suits”


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
“Sorry, Bro”


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 ‘70s Show”, the contrast between the two characters is all the more satisfying for viewers.

#8: Katie Holmes
“The Slutty Pumpkin Returns”


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
“Wait for It”


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
“Of Course”


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 rom-com work she did in the early 2000s.

#5: James Van Der Beek
“Sandcastles in the Sand”


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
“Oh Honey”


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
“Rebound Bro”


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”
“Aldrin Justice”


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.

#1: Britney Spears
“Ten Sessions”


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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