Jimmy Kimmel Live! Weekly Highlights, 17-20 August 2026

It's Jimmy Kimmel's summer break, and each week will have a new guest host. This week, Rosie O'Donnell presented and welcomed guests, including Hannah Waddingham, Ana Gasteyer, The Linda Lindas, Jean Smart, Richard Gadd, Charlie Day, Janelle James, Ashley McBryde, Megan Mullally & Nick Offerman, Shawn Hatosy, and Sydney James Harcourt. Let's take a look at some of the outfits from this week's shows.

Hannah Waddingham

Hannah Waddingham is a British actress best known for her role as Rebecca Welton in the series Ted Lasso. She also appeared in Game of Thrones as Septa Unella and in Sex Education as Sofia Marchetti. Her best-known films include Les Misérables, The Garfield Movie, The Fall Guy, and Mission: Impossible – The Final Reckoning.

On the show, Hannah dressed in a champagne-coloured, sparkly, ribbed, long-sleeved jumper dress with a high mock neck and a calf-length hem. She matched her manicure to her dress and accessorised with large gold hoop earrings and stacked rings.

In this clip, Hannah chats about the latest season of Ted Lasso and her new series with Octavia Spencer, Ride or Die.

Richard Gadd

Scottish actor, comedian, and writer Richard Gadd is famous for creating and starring in the Netflix series Baby Reindeer, based on his self-titled one-man dark comedy show.

During his interview, Richard opted for a burnt orange matching trouser and shacket set. The trousers were wide-legged and straight-cut, and the jacket had an oversized feel. He paired it with an untucked plain white T-shirt and white trainers.

This clip shows Richard discussing his new show, Half Man; his co-star Jamie Bell having a bad haircut for the role; winning Emmys for Baby Reindeer and being nominated again.

Charlie Day

Charlie Day is an American actor and comedian most recognised for playing Charlie Kelly on the dark comedy series It's Always Sunny in Philadelphia, which he also writes and executive produces. He also co-created the Apple TV+ comedy Mythic Quest. His film credits include Pacific Rim, Horrible Bosses and its sequel, Fist Fight, The Super Mario Bros. Movie and The Super Mario Galaxy Movie.

On the programme, Charlie chose a casual look of slim-fitting light-wash jeans, a wine-red shirt with white buttons, and black loafers. He rolled up the sleeves and left the collar unbuttoned for an even more laid-back feel.

In this clip, Charlie discusses how It's Always Sunny in Philadelphia was created, Danny DeVito being in the second season's cast, Guillermo del Toro wanting to be on the show, and filming the 18th season.

Which celebrity outfit was your favourite?

Which outfit on this week's shows was your favourite? Did you like Hannah's sparkly jumper dress? Did you enjoy Richard's matching orange set? Or did you prefer Charlie's red shirt?

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