Chelsea Handler's Hottest Moments Revealed: From Sizzling Bikini Snaps to Comedian's Near-Naked Skiing Adventure
See Chelsea Handler's cheekiest – and hottest – snaps over the years.
Feb. 19 2025, Published 8:30 p.m. ET
A Year-End Wrap-Up
Handler looked back at some moments in her life as she bid goodbye to 2024 in an Instagram post.
In a photo for her year-end wrap-up photoset, Chelsea Handler displayed her slim collarbone as her stylists worked on her hair.
"Byeeeeeeee 2024," she wrote in the caption.
Off on an Adventure
The comic previously dated Jo Koy.
The Chelsea Lately host and her fluffy dog Doug embarked on an adventure across Northern California – including Point Reyes, Bodega Bay, and San Francisco — and captured sweet snaps together.
One striking photo showed Handler wearing a white T-shirt and bikini bottom as she leaned onto her car's trunk.
She said at the time: "We had lots of oysters, lots of beach action (one specifically that left me pantsless) and some cocktails. When he wasn’t acting like he was on crystal meth at the beach, he never stopped taking pictures of me. Like a real lover."
Handler added: "Oh, and I said goodbye to one of my nuggets who is going abroad for a semester because she thinks she’s an independent woman, and she is."
Feeling Hot and Free!
Handler and her family enjoyed a casual morning in Hawaii.
Handler was all smiles while rocking her pink swimsuit during a family getaway in Hawaii.
Part of her caption read: "There is no better feeling than being able to shower all my good luck in this life on my family. Thank you for my shows in Oahu and Maui as well!
"What a joy to be able to travel to such beautiful places while also earning a living. Mahalo!"
Yes, Captain!
The TV host briefly dated rapper 50 Cent in 2011.
In a July 2024 post, the 49-year-old stand-up comedian showed off her assets while on a boat trip in Spain. She accessorized with a white sailor hat and black sunglasses, completing her look.
She said: "Thank you, Mallorca for another trip of great memories, love, some other things, and only one person vomiting from alcohol."
The Cold Didn't Bother Her Anyway
Handler celebrated her 48th birthday with a sexy skiing trip.
Handler marked her special day in 2023 by skiing in a bikini – designed with U.S. and Canadian flags – with goggles, gray gloves, and a black hat.
"This one's for you, Tucker!" she captioned the cheeky snap, seemingly referencing Tucker Carlson after he called her an "aging, deeply unlikeable woman."
How Chelsea Handler Celebrated Independence Day
Chelsea Handler reposted the picture after two years.
All for the LGBTQ+ Community
She previously dated Ted Harbert.
Handler flashed her toned physique in a June 2021 photo. The In the Motherhood star lounged on a large pool float and covered her modesty using a colorful flag, writing, "From my pride float to yours, Happy Pride!"
Looking for Love?
In 2023, Handler debuted a new relationship after her split from Koy.
"Still single," she wrote in the caption of her poolside bikini moment in June 2021.
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Supporting Earth Day
The comedian cheekily went topless for a pool snap.
To mark Earth Day in 2021, Handler uploaded a photo of herself floating in a pool, with two stickers strategically placed to cover her chest area.
"I love mother earth and so do my buoys," she told her followers.
Chelsea Handler Was in Her Golden Hour
She published her first memoir in 2019.
Handler rocked her sleek wet look and black bikini top in a September 2021 selfie.
