Hollywood is in the midst of its two-week Emmy Awards celebration, with the first weekend honoring the plethora of below-the-line talents working on our favorites current shows, as well as a selection of writers, actors and directors. (The bulk of the major nominations will be sorted out during the Primetime Emmys telecast on Monday, September 14.) Kaitlin Olson previously celebrated earning her fourth Emmy nomination, but sadly didn’t come away from the weekend with her first win.
Not that she’s sulking about it or anything. The always hilarious actress took to Instagram to show off just how stylish she and her hubby and Always Sunny co-star Rob Mac were for the ceremony, and of course in a way that poked fun at her unsuccessful streak of non-wins. As the caption put it:
The hair, makeup and wardrobe of a four-time Emmy loser.
Non-recipient would sound so much better than "loser," wouldn't it? A four-time non-recipient almost sounds like it could be a good thing. "I'm a four-time non-recipient of rubella." Not quite the same.
In any case, here's how the beloved comedy couple were decked out for the event, with Rob Mac looking like he's heading up the James Bond-inspired dramatic reboot of Pee-Wee's Playhouse. (Which may not sound like a compliment, but still sincerely is one.)
This marks Kaitlin Olson's third loss in a row for Outstanding Guest Actress in A Comedy for her excellent performances as the daughter of Emmy stalwart Jean Smart, who's taken home the trophy all four times that she's been nominated for her Deborah Vance portrayal. Olson was also nominated in 2020 for Outstanding Actress in a Short Form Comedy or Drama Series for her work in the Quibi crime-comedy series Flipped. (Remember Quibi?)
Upon becoming the non-recipient back in 2024, Olson shared a congratulatory note for winner Jamie Lee Curtis, who was also nomiminated this year. Both actresses, along with fellow Hacks guest actresses Laurie Metcalf, Lauren Weedman and Cherry Jones, were beat out in the category by Betty Gilpin for her hilariously fraught work in Widow's Bay.
Even if it didn't win her an award, at least the world can always enjoy Kaitlin Olson's clown work in Hacks. Which she paid homage to in her Instagram pics with a shot of her in clown makeup as a youth.
It sucks that it’s been a full 12 years since I initially wrote about It’s Always Sunny’s gang being ignored for Emmys, and it sucks that distinction has continued to be true for Olson even outside of Sweet Dee’s immoral hijinks. Maybe next year.
Speaking of, fans won’t get to see Olson’s Morgan returning to the 2026 TV schedule for the third season premiere of High Potential, which isn’t arriving until 2027, but she can absolutely be watched and enjoyed in the 18th season of It’s Always Sunny in Philadelphia, which is currently airing on FX and FXX, and can be streamed via Hulu subscription.
