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Appearance: "Glitter" - Season 6, Episode 9Rachel Bilson plays the Mother's roommate, Cindy. The two briefly date before he realizes that everything he likes about Cindy actually belongs to her roommate. Suits" - Season 5, Episode 12; "Big Days" - Season 6, Episode 1; "Band or DJ?" - Season 8, Episode 13; "How Your Mother Met Me" - Season 9, Episode 16Former Roseanne star Sarah Chalke plays Stella.(Sadly we all know they're not actually related, but isn't it fun to pretend?)Appearance: "Showdown" - Season 2, Episode 20Marshall says the magic words: "Ladies and gentleman, Boyz II Men." Then the boy band appears in the woods and sings "You Just Got Slapped." Classic!
Too bad she later leaves Ted at the altar for her ex-boyfriend Tony.The two even get engaged, but unfortunately that doesn't last.Appearances: "The Stinson Missile Crisis" - Season 7, Episode 4; "Tick Tick Tick" - Season 7, Episode 10; "The Drunk Train" - Season 7, Episode 16; and seven more episodes Wayne Brady plays James Stinson — Barney's gay half-brother.He's a masseuse that plays the guitar, which obviously makes Ted super jealous.Appearance: "Wait For It" - Season 3, Episode 1The actor from Harold & Kumar Go To White Castle and House plays Robin's psychiatrist, who she falls for.