‘It’s Always Sunny in Philadelphia’ Star Kaitlin Olson Jokes She’s a ‘Four-Time Emmy Loser’ and the Internet is Cracking Up

Kaitlin Olson isn’t letting another Emmy loss get in the way of a good joke.

The It’s Always Sunny in Philadelphia star poked fun at her awards record on Instagram after attending the Emmys on Sunday, September 6, alongside her husband Rob Mac (real name Rob McElhenney).

“The hair, makeup and wardrobe of a four-time Emmy loser,” Olson, 51, joked in the caption the following day before crediting the team behind her red carpet look.

Olson wore a strapless white gown for the occasion, and her Insta carousel included a red carpet shot showing off the look, as well as photos with Mac and The White Lotus star Leslie Bibb. She hilariously ended the carousel with a childhood photo of herself in clown face paint.

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“GORGEOUS !!! 🔥 (you won in my mind where i live in a constant state of delusion),” one fan wrote in the comments.

Another shared, “if it makes you feel better my roommate and i stayed up on EST timezone and waited for your category. you’re the winner in our hearts!!!!!”

“Yall are 18 time Emmy winners in our books!” said a third.

The “four-time Emmy loser” line is technically accurate. Olson has received four career Emmy nominations, three of which recognized her guest performance as DJ Vance on Hacks in 2022, 2024, and now 2026. Her first came in 2020 for the short-form comedy Flipped. This year, she lost the guest actress category to Widow’s Bay star Betty Gilpin.

READ MORE: Rob McElhenney Reveals Why Dating Kaitlin Olson Was Worth the Risk Despite Being ‘Frowned Upon’

Olson’s work on Hacks has also taken on an especially personal meaning. While filming the show’s fifth and final season, her father, Don, became seriously ill following complications from surgery. Olson balanced filming with traveling to be with him as his condition worsened.

One of his final opportunities to watch his daughter perform came courtesy of Hacks. Don saw Olson’s DJ compete alongside Jean Smart’s Deborah Vance in the comedy’s elaborate Amazing Race-inspired episode before his death in May. “And he loved it,” Olson said to Vanity Fair of her father’s reaction to the episode.