These celebrity appearances were legen — wait for it — dary.

How I Met Your Mother’s 25 most memorable guest stars

These celebrity appearances were legen — wait for it — dary.

By Madeline Boardman

Madeline Boardman

Madeline Boardman is a former digital features director at **. She left EW in 2017.

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and Kevin Jacobsen

May 11, 2026 2:00 p.m. ET

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Britney Spears as Abby, Kyle MacLachlan as the Captain, and James Van Der Beek as Simon on 'How I Met Your Mother'. Credit:

Monty Brinton/CBS via Getty; Richard Cartwright/CBS via Getty; Cliff Lipson/CBS via Getty

*How I Met Your Mother* became one of the only traditional multi-camera sitcoms to find long-term success in the wake of *Friends*. The CBS comedy, which explored the love lives of Ted (Josh Radnor) and his friends in New York City, aired for nine seasons from 2005 to 2014, and drew praise for its witty writing and game ensemble.

While it largely focused on Radnor and his costars — Jason Segel, Cobie Smulders, Neil Patrick Harris, and Alyson Hannigan — the show found plenty of room for guest stars, too. From TV legends like Alan Thicke to pop stars like Britney Spears and Katy Perry, a surprising number of big names populated the series over the years, most of them fitting in relatively well with the gang. Ahead, we're highlighting our favorite *HIMYM* guest stars, from the great to the (wait for it) legendary.

Britney Spears

Britney Spears as Abby and Josh Radnor as Ted Mosby on 'How I Met Your Mother'. Monty Brinton/CBS

The Princess of Pop brought her star power to *How I Met Your Mother* for two episodes in 2008. She appeared as Abby, a receptionist at dermatologist Stella's (Sarah Chalke) office with a soft spot for Ted.

James Van Der Beek

Cobie Smulders as Robin Scherbatsky and James Van Der Beek as Simon Tremblay on 'How I Met Your Mother'. Cliff Lipson/CBS

James Van Der Beek first dropped by *How I Met Your Mother* in 2008. The actor played Simon Tremblay, Robin's (Cobie Smulders) former Canadian love interest, and returned to the show for two episodes in 2013.

Jennifer Morrison as Zoey Pierson, Katy Perry as Honey, Josh Radnor as Ted Mosby, Alyson Hannigan as Lily Aldrin, and Neil Patrick Harris as Barney Stinson on 'How I Met Your Mother'. Sonja Flemming/CBS via Getty Images

In 2011, Katy Perry stopped by *How I Met Your Mother*, playing a character known only as Honey. She appeared as an oblivious, albeit beautiful woman, whose lack of awareness often elicited a response of, "Oh, Honey..."

Jorge Garcia

Alyson Hannigan as Lily Aldrin, Josh Radnor as Ted Mosby, Cobie Smulders as Robin Scherbatsky, Jorge Garcia as Steve 'Blitz' Henry on 'How I Met Your Mother'. Eric McCandless/CBS

The same year that *Lost* wrapped, Jorge Garcia debuted on *How I Met Your Mother* as Steve "the Blitz" Henry. A college friend of Ted and Marshall's (Jason Segel), the Blitz's bad luck always made him miss out on the fun.

Regis Philbin

Regis Philbin as himself and Neil Patrick Harris as Barney Stinson on 'How I Met Your Mother'. Monty Brinton/CBS via Getty Images

Regis Philbin graced *How I Met Your Mother* with his presence for one episode in 2008. The star played himself, brushing shoulders with Marshall as he hunted for a perfect cheeseburger.

Joe Manganiello

Joe Manganiello as Brad Morris and Jason Segel as Marshall Eriksen on 'How I Met Your Mother'. Richard Cartwright/CBS

Joe Manganiello did a seven-episode stint on *How I Met Your Mother* as Brad Morris. Appearing over the course of six years, the actor played Marshall's friend from law school.

Neil Patrick Harris as Barney Stinson, Alan Thicke as himself, April Bowlby as Meg, and Cobie Smulders as Robin Scherbatsky on 'How I Met Your Mother'. Monty Brinton/CBS via Getty Images

The *Growing Pains* alum dropped by *How I Met Your Mother* five times during the show's run. A fellow Canadian, Alan Thicke was shown as a friend and former collaborator of Robin's, first appearing with her in a music video for the song “Sandcastles in the Sand” from her teen pop star days.

Tim Gunn as himself and Josh Radnor as Ted Mosby on 'How I Met Your Mother'. Richard Cartwright/CBS via Getty Images

Tim Gunn played himself on *How I Met Your Mother*, appearing in a handful of episodes over the course of four years. The *Project Runway* star found his place in the gang as Barney's (Neil Patrick Harris) emergency tailor for his beloved suits.

Rachel Bilson

Josh Radnor as Ted Mosby and Rachel Bilson as Cindy on 'How I Met Your Mother'. Cliff Lipson/CBS

A few years after wrapping her run on *The O.C.*, Rachel Bilson played Cindy on *How I Met Your Mother*. Debuting in two 2010 episodes, Bilson popped back up in 2013 and 2014, appearing as Ted's former fling and his future wife's roommate.

John Lithgow

John Lithgow as Jerome Whittaker and Neil Patrick Harris as Barney Stinson on 'How I Met Your Mother'. Sonja Flemmming/CBS

John Lithgow joined *How I Met Your Mother* in 2011 as Jerry Whitaker, Barney's long-absent father. The actor returned to the show for 2013 and 2014 episodes, reuniting with his onscreen son.

Laura Prepon

Josh Randor as Ted Mosby and Laura Prepon as Karen on 'How I Met Your Mother'. Sonja Flemming/CBS

Laura Prepon popped up in three *How I Met Your Mother* episodes between 2009 and 2010. The *That '70s Show* alum played Karen, Ted's polarizing college girlfriend.

Martin Short

Martin Short as Garrison Cootes and Josh Radnor as Ted Mosby on 'How I Met Your Mother'. Ron P. Jaffe/Fox

Martin Short played Garrison Cootes on *How I Met Your Mother* for three episodes in 2011 and 2012. His character is Marshall's boss at Honeywell & Cootes.

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Bryan Cranston

Bryan Cranston as Hammond Druthers and Josh Radnor as Ted Mosby on 'How I Met Your Mother'. CBS

In the midst of his turn as *Breaking Bad*'s Walter White, Bryan Cranston played Ted's eccentric boss, Hammond Druthers, for three episodes of *How I Met Your Mother*.

Danica McKellar

Danica McKellar as Trudy on 'How I Met Your Mother'. CBS

Former child star Danica McKellar found her spot on *How I Met Your Mother* as Trudy. She played one of Ted's love interests in two episodes.

Enrique Iglesias

Enrique Iglesias as Gael, Cobie Smulders as Robin Scherbatsky, and Alyson Hannigan as Lily Aldrin on 'How I Met Your Mother'. Cliff Lipson/CBS

Singer Enrique Iglesias flexed his acting muscles in 2007 as Gael on *How I Met Your Mother*. His character was Robin's rebound guy, a significant shift from Ted.

Will Forte as Randy Wharmpess and Neil Patrick Harris as Barney Stinson on 'How I Met Your Mother'. CBS

Will Forte brought Randy Wharmpess to *How I Met Your Mother*, playing Barney's unimpressive co-worker for two episodes in 2008 and 2010.

Katie Holmes

Katie Holmes as Naomi and Josh Radnor as Ted Mosby on 'How I Met Your Mother'. Monty Brinton/CBS

After years of mystery, the Slutty Pumpkin finally revealed herself in *How I Met Your Mother*'s seventh season. Named Naomi, the character was played by Katie Holmes.

Jennifer Lopez

Jennifer Lopez as Anita Appleby and Neil Patrick Harris as Barney Stinson on 'How I Met Your Mother'. Monty Brinton/CBS

Jennifer Lopez made an appearance in *How I Met Your Mother*'s fifth season. The multihyphenate played Anita Appleby, a relationship expert whom Barney attempts to woo.

Bob Barker as himself and Neil Patrick Harris as Barney Stinson on 'How I Met Your Mother'. Cliff Lipson/CBS

Bob Barker showed up on *How I Met Your Mother* in 2007, playing himself. He found his way into the narrative after Barney became convinced that the game show host was his father.

Nicole Scherzinger

Cobie Smulders as Robin Scherbatsky and Nicole Scherzinger as Jessica Glitter on 'How I Met Your Mother'. Ron P. Jaffe/CBS

Nicole Scherzinger lent her pop star chops to *How I Met Your Mother* in 2010. The performer played Jessica Glitter, Robin's estranged best friend from Canada.

Carrie Underwood

Carrie Underwood as Tiffany and Josh Radnor as Ted Mosby on 'How I Met Your Mother'. Richard Foreman/CBS

*American Idol* season 4 winner Carrie Underwood landed an acting role in 2010 thanks to *How I Met Your Mother*. The country crooner played Tiffany in one episode, a woman who's kept Ted on the hook for weeks.

Lin-Manuel Miranda

Lin-Manuel Miranda as Gus on 'How I Met Your Mother'.

Two years before launching the record-breaking blockbuster musical *Hamilton*, Lin-Manuel Miranda appeared in the final season of *HIMYM*, fittingly playing a bus passenger who performs an impromptu rap about Canada. While the other passengers burst into applause, Marshall humorously deadpans, "Show-off."

Mandy Moore as Amy on 'How I Met Your Mother'.

A few years into her movie career, Mandy Moore guest-starred in *How I Met Your Mother*'s season 3 premiere. The singer-actress played against type as a tattooed, rebellious woman named Amy, whom Ted briefly dates and leads him to get his infamous lower back tattoo.**

Heidi Klum as herself, Neil Patrick Harris as Barney Stinson, and Josh Radnor as Ted Mosby on 'How I Met Your Mother'.

Heidi Klum took some time off from hosting *Project Runway* to appear in a season 3 episode of *How I Met Your Mother*. The model-host made a cameo as herself when Ted and Barney attended a Victoria's Secret Fashion Show after-party, giving Barney advice on how to get over "the yips."

Kyle MacLachlan

Kyle MacLachlan as the Captain on 'How I Met Your Mother'.

Richard Cartwright/CBS via Getty

*Twin Peaks* alum Kyle MacLachlan was one of *HIMYM*'s most important guest stars, appearing in seven episodes across three seasons as "the Captain," first appearing in season 6 as a wealthy, intimidating figure whose wife was having an affair with Ted; he later hired Lily as an art consultant.**

- How I Met Your Mother

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