Top 10 Funniest Guest Stars in How I Met Your Mother

1. Britney Spears as Abby

Did anyone expect that the Princess of Pop would be such a hoot in How I Met Your Mother? Spears played Abby, the receptionist at Stella's dermatology clinic, who develops a massive crush on Ted. She was a hurricane of hilarity, from her overly flirtatious attempts to get Ted's attention to her childish antics when she felt ignored. And who can forget the hilarious moment when she teamed up with Barney, thinking he was Ted's "wingman"? If Spears's comedic timing was a song, it would surely top the charts!

2. Bryan Cranston as Hammond Druthers

Before he started breaking bad as Walter White, Bryan Cranston was making us break into laughter as Hammond Druthers in HIMYM. As Ted's pompous, egotistical boss, Cranston delivered a performance that was equal parts hilarious and cringeworthy. Remember the episode where he makes Ted build a ridiculously phallic building, completely oblivious to its shape? Or when he's down on his luck and winds up sleeping on Ted's couch, eating his food, and mooching off him like a leech with a design degree? Cranston's portrayal of Druthers was so funny; it could have been an Emmy-winning sitcom on its own.

3. Sarah Chalke as Stella

Sarah Chalke, better known as the lovable Elliot in "Scrubs," left us in stitches as Stella, Ted's dermatologist-turned-fiancée. From removing Ted's regrettable lower back tattoo (it's not a tramp stamp, it's a lower back tattoo!) to her vehement dislike for "Star Wars" (blasphemy!), Chalke brought a unique blend of charm and wit to the character. And the twist where she leaves Ted at the altar to go back to her ex? Sure, it was heartbreaking, but come on, it was also chuckle-inducing in a 'laughing-at-you-not-with-you' sort of way.

4. Kyle MacLachlan as The Captain

Sailing into the show like a breath of fresh (sea) air, Kyle MacLachlan as The Captain was an absolute comedic anchor (pun very much intended!). The wealthy, eccentric, and often intimidating ex-husband of Zoey was a whirlwind of hilarity. From his frighteningly intense eyes to his rather obsessive love of boats and the sea, The Captain was like a naval-themed rollercoaster that leaves you breathless from laughter. Remember when he interrogates Ted about touching his wife's "six-foot-eight, hard as a rock" antique? The innocent misunderstanding becomes a comedic goldmine, thanks to MacLachlan's brilliant acting. If there were an award for being both funny and scary simultaneously, The Captain would surely win hands down.

5. Katy Perry as Honey

Oh, honey! Or should we say, oh Katy Perry? Perry graced the show as Zoey's naïve cousin, Honey, who was so gullible, she made a puppy look like a seasoned skeptic. No one remembers her real name (or if they ever knew it in the first place), but her cluelessness provided some of the show's funniest moments. Who can forget when she thought 'eating a sandwich' meant actual sandwiches or when she actually believed Barney was Neil Armstrong? Her innocence and naivety were so hilariously sweet, you couldn't help but laugh out loud, all while muttering, "Oh, honey!"

6. Jennifer Lopez as Anita Appleby

Jennifer Lopez swapping her 'Jenny from the Block' persona for a no-nonsense, anti-flirtatious author was a stroke of comedic genius. As Anita Appleby, Lopez was a force to be reckoned with, giving Barney a taste of his own medicine. The sheer hilarity of seeing Barney, the infamous womanizer, squirm under Anita's 'Of Course You're Still Single, Take a Look at Yourself, You Dumb Slut' rules was a treat. And when Anita falls for Barney's playbook strategy, the reversal is so absurdly funny, it's likely to cause a full-on belly laugh.

7. James Van Der Beek as Simon Tremblay

James Van Der Beek's portrayal of Simon Tremblay, Robin's ex-boyfriend from Canada, was so ridiculously hilarious it should have been declared a national treasure...of Canada, of course. His acid-washed jeans, his brazen overconfidence, and the gloriously iconic 'Murder Train' song, all worked together to make Simon one of the funniest guest characters on HIMYM. His uncaring attitude and dismissive treatment of Robin were made all the funnier by Robin's inexplicable attraction to him. Simon might be a jerk, but Van Der Beek's comedic brilliance turned him into a jerk we all love to laugh at.

8. Wayne Brady as James Stinson

As Barney's gay, African-American, half-brother, Wayne Brady's James Stinson was like a perfectly crafted comedy bomb that exploded in fits of laughter every time he was on screen. From his smooth charm, his shared love for suits with Barney, to his knack for bursting into song at any moment, James was pure comedic gold. And let's not forget the dramatic revelation of who his father was – no, not Bob Barker, but none other than Sam Gibbs, played by the legendary Ben Vereen! Watching Brady and Neil Patrick Harris playing off each other was like watching a comedic ballet, elegant and uproariously funny.

9. Laura Prepon as Karen

Laura Prepon portrayed Ted's pretentious college girlfriend who was as hilarious as she was infuriating. From her absurdly pretentious opinions ("Guns N' Roses is so mainstream. Do you know who really had something to say? Toto.") to her infidelity and her bizarre fascination with Pablo Neruda's poetry, Karen was a character you loved to hate and laughed at all the while. Prepon's comedic timing and knack for playing funny, offbeat characters shone through in her portrayal of Karen, making her one of the most memorable guest stars on the show.

10. Enrique Iglesias as Gael

Remember when Enrique Iglesias stepped away from the microphone and stepped into the hilariously charming shoes of Gael (or was it Kyle?). As Robin's post-Ted rebound, Gael was a sexy, sensitive, spiritual masseur, with an accent that could melt butter. But the funniest aspect of his character was how he was the polar opposite of Ted, causing both amusement and annoyance among the gang. Whether it was his guitar playing, his endless anecdotes about his travels, or his intriguingly mysterious job, Gael brought a unique flavor of comedy to the show that was as funny as it was refreshing.