How I Met Your Mother may have been about Ted Mosby’s quest to find true love, but before that happened there was no shortage of gorgeous women who have entered into the life of Mosby and friends. Granted, when you consider one of his best friends was Barney Stinson are you really surprised?
Whether attempting to woo the affections of one of the gang, or just blessing us with their presence, below we have the 15 most beautiful guest stars to appear in the series.
Fans who didn’t stay with the series after falling in love with the first few seasons may be amazed at some of the beautiful women that came through the series towards the end (Ashley Benson anyone?), including who they cast as the famous slutty pumpkin.
Whether the characters stayed around for a few episodes like Britney Spears and Rachel Bilson or you could blink and miss them like Malin Akerman and Mandy Moore, these 15 women all put their touch on the series; even if one of them realized she’d rather be touched by women.
Perhaps Ted’s search for The One wasn’t so bad after all!
15. Anne Dudek
Which Episode? “Return of the Shirt” Season 1, Episode 4, “Say Cheese”, Season 5, Episode 18.
When you consider that Anne Dudek ended up getting a fairly regular role on the television series Mad Men, you can imagine that she must be pretty thankful that her bid to be the mother ended up being unsuccessful.
Ted previously went on a date with Natalie (Dudek’s character) but broke up with her (over her answering machine no less) on her birthday. Yet he’s still able to re-kindle their affection and even finds himself happy in their relationship until he realizes she isn’t the one for him and breaks it off again, and as fate would have it, it also ends up being on her birthday again.
Understandably, the episode ends with her laying the smackdown on Ted. As a fun fact, Dudek also plays Precious (Paul Rudd‘s short-term girlfriend) on Friends.
14. Mandy Moore
Which Episode? “Wait For It” Season 3, Episode 1.
The end of season 2 wrapped up with Ted and Robin going their separate ways, so understandably the start of season 3 ended up with Ted attempting to get over his slump and find someone new to give his affections to.
Who better than Mandy Moore who elects to leave her conservative image at the door as she plays the closest thing the series has to a badass, as she steals liquor, has tattoos and is generally fairly wild (including getting all up in Ted’s face.)
13. Heidi Klum
Which Episode? “The Yips” Season 3, Episode 10.
You may think that Barney Stinson was always amazing in bed, and if you asked him prior to this season 3 episode, he probably would agree with you. Yet sadly for Barney, in “The Yips” he learns that the first ever woman he took to bed, lied (or more accurately, heavily used sarcasm) when describing his prowess.
The realization is a blow to Barney’s confidence and prevents him from successfully flirting with women, which he called the Yips.
This becomes all the more frustrating when he attends the Victoria’s Secret Fashion Show. While there we get to run into Heidi Klum who convinces Barney to go and re-sleep with the first ever person he slept with to regain his confidence.
12. Britney Spears
Which Episode? “Ten Sessions” Season 3, Episode 13 and “Everything Must Go” Season 3, Episode 19.
Barney Stinson has a tendency to sleep with a lot of women and never call them again. That behavior catches up with him when he decides to bed the crazy (albeit crazy hot) Abby, Stella’s receptionist, and then never call her again.
It leads to Abby stalking the women that Barney is attempting to seal the deal with and then warning them before he gets the chance to sleep with them. When she’s caught, we get another hilarious episode in which Abby and Barney patch things up and pretend to be in a relationship to taunt Ted who Abby was in love with and Barney was feuding with.
11. Laura Prepon
Which Episode? “Sorry Bro” Season 4, Episode 16, “The Front Porch” Season 4, Episode 17 and “Say Cheese” Season 5, Episode 18.
When it comes to the person that you choose to spend your life with, one of the most important factors for you may be how they interact with your friends. When you consider how close the gang was, you can understand this was absolutely a factor.
Sadly for fans of Laura Prepon, her character of Karen was far from the most heartwarming and not only hated on the rest of the gang but cheated on Ted on multiple occasions and that’s hardly what you want.
While Karen only appears in the 3 episodes, she does make an appearance (either by name or flashback/photograph) in “Arrivederci, Fiero”, “How I Met Everyone Else”, “The Rough Patch”, “Twin Beds”, “Last Words” and “Challenge Accepted”.
10. Stacy Keibler
Which Episode? “Girls Versus Suits” Season 5, Episode 12.
When it comes to tough decisions that Barney has to make, one of the most vexing came in the episode “Girls Versus Suits” when he learns that if he’s going to be able to bed Stacy Keibler, he’s going to have to ditch his suits.
This gives viewers the rare chance to see Barney leave the suits at home, at least temporarily and even includes a great musical number in which Barney sings about how he’d always choose suits over a girl. Granted he then lies to her, says he’s getting rid of them and sleeps with her anyway, but what else would you expect from Barney?
9. Rachel Bilson
Which Episode? “Girls Versus Suits” Season 5, Episode 12, “Big Days” Season 6, Episode 1, “Band or DJ?” Season 8, Episode 13 and “How Your Mother Met Me” Season 9, Episode 16.
Rachel Bilson may only appear in 4 episodes so we wouldn’t blame you if you didn’t easily remember her role, but are you really going to hate on us for including her in our list? Especially when you consider she is the roommate of ‘the mother’!
While Ted takes his shot at winning over Bilson, including getting back to her apartment (where he fawns over items belonging to the mother) we find out in her season 6 appearance that Bilson has learned that she prefers the touch of a woman!
8. Carrie Underwood
Which Episode? “Hooked” Season 5, Episode 16.
Carrie Underwood isn’t the only drop dead gorgeous woman to make an appearance in season 5, but she is the only one to make an appearance while holding an adorable teacup pig so we definitely have to give her credit for that.
In an episode entitled “Hooked”, the gang reflects on past crushes that they have kept on the hook (never fully telling them they’d never end up together) or were “on the hook” for (would bend over backward to help out, even though never hooked up).
Essentially, Carrie showed up to solidify to audiences what the friend zone is and to declare Ted the mayor of it. Though when you’re as beautiful as Carrie, you can understand why Ted would want to stick around.
7. Jennifer Lopez
Which Episode? “Of Course”, Season 5, Episode 17.
Can you imagine being Barney Stinson, going on a date with Jennifer Lopez and then not being able to seal the deal? That’s the premise around Lopez’s brief time on the show as she plays a character who writes a self-help book entitled “Of Course You’re Still Single, Take A Look at Yourself, You Dumb Slut” that is centered around a woman having the power and confidence to say no to a man when he attempts to sleep with her on the first date.
The episode ends up being a nice bit of growth for Barney who ends up passing on the opportunity to eventually sleep with Anita in order to help preserve his friendship which Robin which was suffering at the time.
6. Judy Greer
Which Episode? Season 5, Episode 23.
Your favorite role of Judy Greer’s may be when she voices Cheryl on the television series Archer but there is also no reason to be hating on when movies and television shows allow the beautiful Greer to step in front of the camera.
It’s Ted who wins over her affections in the movie “The Wedding Bride” that also centers around the idea the gang learning to deal with their own personal baggage (in Ted’s case, he was left at the altar and then it was turned into a movie.)
5. Malin Akerman
Which Episode? “The Wedding Bride” Season 5, Episode 23.
There isn’t just one, but two gorgeous women that guest star in the season 5 episode “The Wedding Bride”. While we get to know Judy Greer outside of the screen, in the fictional movie The Wedding Bride that Ted and Greer go and see, the role of Stella is played by the beautiful Malin Akerman.
While Akerman may not have as many lines as a typical guest role, we definitely aren’t going to blame the casting department when you consider they were trying to just find a beautiful blonde to fit the role. Plus we also get to see Chris Kattan of Saturday Night Live fame play the role of Ted and is one of the funnier cameos of the series.
4. Nicole Scherzinger
Which Episode? “Glitter” Season 6, Episode 9.
One of the best running jokes throughout the series is the element of Robin Sparkles, aka Robin’s Canadian teenage pop star alternate identity. While you may love the song “Let’s Go To The Mall” or “Sandcastles in the Sand”, fans learned even more about the character in the episode “Glitter” in which the gang discovers that she used to appear on a Canadian television show as well.
The show is not only hilarious and filled with sexual innuendos, but also lets us meet her former friend and costar Jessica Glitter who is played by the beautiful Nicole Scherzinger.
3. Katy Perry
Which Episode? “Oh Honey”, Season 6, Episode 15.
Katy Perry may be one of the most recognizable names of anyone on our list, but when it came to naming the character on the show the writers instead elected to just call her “Honey”, a nickname earned for her incredibly naive personality.
While she was originally intended to be taking a trip downtown with TMosby, it’s Barney that ends up wooing her affections enough to get her back to the bedroom, where unfortunately for him, unresolved father issues prevent the action from getting too X-Rated.
2. Katie Holmes
Which Episode? “Slutty Pumpkin Returns”, Season 7, Episode 8.
You aren’t a fan of How I Met Your Mother if you’re not enthralled with the story of the “slutty pumpkin” which started out in season 1. Ted infamously would spend his Halloweens awaiting the beautiful woman who once captured his heart while wearing a pumpkin costume, but tragically lost her phone number.
The series finally got around to revealing the identity of the pumpkin in season 7 and understandably with quite the build-up, they wanted to cast someone great in the role. Holmes excels in one of the funnier episodes of the series and even though she’s definitely not the dream girl that Ted had been hoping for, she’s still a welcome addition for her brief stay on the show.
1. Ashley Benson
Which Episode? “Ring Up” Season 8, Episode 14.
When you sleep with someone, one of the most important deciding factors may be that you… y’know, “like” the person. That definitely wasn’t the rule for Barney, but for Ted, it definitely seemed to ring true.
Yet in the episode “Ring Up”, Ted finds himself going on dates with the 20-year-old Carly because she’s very attractive. While he initially says he won’t sleep with her, Barney convinces him that he should give her another shot and Ted ends up sleeping with her after hearing her R2-D2 ringtone.
The episode takes a humorous turn when it turns out that she is actually Barney’s half-sister.
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