After guest roles on The Equalizer in 1985, Tales from the Darkside in 1988, and a 1994 ep of The X-Files as a seismologist infected by an evil organism, Whitford joined ER for two episodes, including the show's most famous episode ever, "Love's Labor Lost."
The 1995 Emmy-winning episode featured Whitford as an expectant father whose wife comes in to see Dr. Greene and is mis-diagnosed with a bladder infection instead of pre-eclampsia. She later dies after childbirth, leaving Sean alone with the baby and all of us with some serious heartbreak.
The description of this show, in which Whitford starred with Peter Gallagher and Mitch Rouse, tells you everything you need to know: "Three divorced men get thrown back into the bachelor life. With nothing left but each other, Michael, Phil, and Andy form an exclusive club and embark on a new phase of their existence. Someday, they might comprehend the mysteries of women, love and, golf. Until then, they'll continue carrying on The Secret Lives of Men."
Just a little show you might not have heard of. Whitford played Josh Lyman, White House deputy chief of staff to President Bartlet, a role that won him three Emmys in 2001, 2002, and 2003.
Aaron Sorkin followed up The West Wing with Studio 60 on the Sunset Strip, a show about a live comedy show sorta similar to Saturday Night Live. Whitford played Danny Tripp, former segment producer and new executive producer on the show who's BFFs with writer and fellow new EP Matt Albie, played by Matthew Perry. Studio 60 tragically(?) only lasted one season.
Whitford starred opposite Colin Hanks in a show about the old-fashioned mustachioed detective (Whitford) working with a new, young, ambitious partner (Hanks). Fox canceled the show and that mustache after just one season.
After guest roles on The Mentalist, Go On, Law & Order: LA, and Parks and Recreation, Whitford guest starred in the Showtime series as Abraham, described ahead of time as "a powerful, well-dressed and sophisticated gay man who is a political activist." We ended up meeting him when Frank (William H. Macy) inadvertently becomes the leader of a gay rights movement in season three.
We genuinely still think about this one season gem on a regular basis. Whitford played new husband to Kate (Malin Akerman), and ex-husband to both Diane (Marcia Gay Harden) and Jackie (Michaela Watkins). The show was really about the women and their kids, so Whitford was just a perfectly nice but ever so slightly boring lawyer named Pete. And it was great.
This show came after guest roles on Drunk History and Law & Order: SVU.
Whitford starred alongside Steve Coogan and Kathryn Hahn in this show about a man (Coogan) who struggles to be truly happy so he settles for "happyish."
Jake Peralta's (Andy Samberg) slightly no-good dad turned out to be none other than Whitford, who played Roger Peralta as a lovable goof despite also being somewhat of a conman and a womanizer. His last appearance was in 2017 so it feels like time for another visit from dad, huh?
Whitford spent two episodes on Mom as Mitch, a guy who was pretty much a lot of bad news for Christy and Bonnie.
Whitford won in 2015 and was nominated in 2016 at the Emmys for his guest role on the Amazon series. He's played two characters, including closet transvestite Marcy and "the Isaac Newton of sex," Magnus Hirschfield, in season two flashbacks to 1930s Berlin.
Whitford stars alongside Steve Zahn, Lamore Morris, and John Karna in this Nat Geo miniseries about the dotcom boom in the '90s, with Whitford playing the CEO of Netscape.
This is the role that won Whitford his 2019 Emmy for outstanding guest actor. He plays Commander Lawrence, a powerful man in Gilead dealing with some guilt over what he's done. It's a bit of a jump over to choir director, but it's not as if Whitford hasn't done it before!