Movies Gallery 21 of the best How I Met Your Mother guest stars Meet the best celeb appearances on the sitcom. By Madeline Boardman Madeline Boardman Madeline Boardman is a former digital features director at Entertainment Weekly. She left EW in 2017. EW's editorial guidelines Updated on July 19, 2022 10:20AM EDT Trending Videos Close this video player 01 of 21 Britney Spears 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 (Josh Randor). 02 of 21 James Van Der Beek 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. 03 of 21 Katy Perry 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..." 04 of 21 Jorge Garcia 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. 05 of 21 Regis Philbin 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. 06 of 21 Joe Manganiello 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. 07 of 21 Alan Thicke 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, Thicke was shown as a friend and former collaborator of Robin's, first appearing with her in a music video from her teen pop star days. 08 of 21 Tim Gunn 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. 09 of 21 Rachel Bilson 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. 10 of 21 John Lithgow 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. 11 of 21 Laura Prepon 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. 12 of 21 Martin Short 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. 13 of 21 Bryan Cranston 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. 14 of 21 Danica McKellar CBS The former child star found her spot on How I Met Your Mother as Trudy. She played one of Ted's love interests in two episodes. 15 of 21 Enrique Iglesias Cliff Lipson/CBS The singer 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. 16 of 21 Will Forte 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. 17 of 21 Katie Holmes 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. 18 of 21 Jennifer Lopez Monty Brinton/CBS Jennifer Lopez made an appearance in How I Met Your Mother's fifth season. The star played Anita Appleby, a relationship expert whom Barney attempts to woo. 19 of 21 Bob Barker 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. 20 of 21 Nicole Scherzinger 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. 21 of 21 Carrie Underwood Richard Foreman/CBS 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.