A Complete Guide to Celebrities at the Milano Cortina Winter Olympics 2026

The Winter Games have delivered record-breaking runs and glittering red carpets, but it was the celebrity moments that had everyone refreshing their feeds.

When Milano Cortina 2026 officially kicked off in early February, A-listers from every corner of entertainment and sports descended on Italy.

Yet amid all the glamour, whispers of concern about one global singer's opening ceremony performance added an unexpected layer of intrigue that kept fans watching closely. And one normally tough influencer surprised everyone by bawling his eyes out!

Check out the appearances of all your favorite stars at one of the most important sporting events in the world!

Snoop Dogg

Before he even touched down in Italy, Snoop Dogg had already made Olympic history.

On December 10, 2025, the United States Olympic & Paralympic Committee announced that Snoop Dogg joined Team USA as its first Honorary Coach, a volunteer role designed to celebrate and support America's athletes off the field of play, according to the official USOPC announcement.

In this position, he became part of the Team Behind the Team, working alongside staff, coaches, medical experts, and administrators helping athletes chase their dreams.

Known for his passion for mentorship and community, he brought humor and heart to the Games.

Regarding his new role, the rapper said:

"Team USA athletes are the real stars—I'm just here to cheer, uplift and maybe drop a little wisdom from the sidelines. This team represents the best of what sport can be: talent, heart and hustle. If I can bring a little more love and motivation to that, that's a win for me."

And he did not just talk about love and motivation. He showed it.

On February 14, it was reported that he ordered food at a local bar but could not pay at the time because of an issue with his credit card.

According to NBCLA, the bar owners' daughter told the press that her parents let him take the meal anyway, and the very next day he returned, paid for it, and gifted the family five tickets to the men's snowboard halfpipe final.

Then there was his unmistakable presence at the venues.

Snoop attended multiple events, including the curling mixed doubles round robin match between Team United States and Team Canada on February 6 at the Cortina Curling Olympic Stadium.

He later appeared at the figure skating women single skating short program on February 17 at the Milano Ice Skating Arena, where he was seen alongside U.S. ice skater Ilia Malinin and Martha Stewart as they commented for NBC.

Furthermore, his wardrobe became a storyline of its own.

He consistently wore bold outfits in USA team colors and themes, with some pants reading "Coach Snoop." In certain looks, he even sported the names of athletes like American bobsledder Kaysha Love, turning his fashion into a literal show of support.

And while Snoop's energy felt playful, the next celebrity brought a deeply personal perspective to the ice.

Simone Biles and Jonathan Owens

She understands pressure in a way few people ever will.

On February 13, Simone Biles attended the men's figure skating final at the Milano Ice Skating Arena, where Malinin finished outside the medals. Speaking to Olympics on February 17 in Milano, Biles admitted, "I was really worried about how his mental health was going to be."

"When you're expected to skate a performance of your lifetime and you don't deliver, I worry how that affects his mental and how the world is going to view that," she continued. "I've been through that firsthand and so I really went into protection mode."

Biles arrived in Milano while partnering with Mandarin Oriental to advocate for health and wellness, but her presence in the stands spoke volumes.

She and her husband, Jonathan Owens, were spotted at several skating events, typically dressed in sporty jackets, with Owens frequently representing Team USA.

And Milan gave Owens a wild story to tell.

On February 15, he wrote on X, "Not somebody just tried to snatch my shopping bag in Milan, force of habit i had it tied around my hand so he couldn't get it and took off running immediately….but still crazy."

From mental health advocacy to near handbag drama, their Olympic experience had range. But no moment sparked more chatter than the opening ceremony performance that had fans both praising and worrying.

Mariah Carey

She was announced as the first major music icon of the opening ceremony, scheduled for February 6 at the San Siro Olympic Stadium in Milano.

Recognized worldwide for her unmistakable voice and cross-generational musical legacy, she was described as embodying the emotional spirit of the Games.

Carey arrived in Milan for the event on February 2 wearing an all-black airport look that featured a short dress, a long coat, and thigh-high boots. For the actual performance, she leaned fully into Italian glamour.

In homage to the Games' northern Italian setting, she wore a custom Roberto Cavalli white bustier satin gown designed by Fausto Puglisi.

The fitted silhouette with a mermaid train was embroidered with Swarovski embellishments and finished with an ostrich feather stole, while high jewelry by Levuma and flowing waves completed the look.

During the ceremony, she opened with a tribute to Italy through Domenico Modugno's "Nel Blu, dipinto di Blu" and then energized the stadium with her song "Nothing Is Impossible."

Still, not everyone focused solely on the vocals. Some were concerned for her because she didn't seem to move much while singing.

Under the Instagram post, one person wrote, "What's happening with her? She barley moves? I'm worried [sic]." Another commented, "I love you Mariah but you looked so uncomfortable and emotionless. Qué?"

And then there were the devoted fans who pushed back, with one declaring, "Greatest voice of all time🗣️🦋🌍👸🏼."

But as that conversation unfolded online, another stylish duo was quietly stealing scenes off the ice.

Stanley Tucci

If there was a masterclass in polished Olympic hosting, Stanley Tucci delivered it.

He teamed up with Snoop Dogg for NBC in a segment where the two hit a bar in Italy and discussed their signature styles. Snoop wore a jacket featuring himself with the phrase "Snoop Dogg Searching for Stanley Tucci," complete with Italian monuments.

Tucci opted for a USA cardigan layered over a dark turtleneck sweater. The two enjoyed drinks, reflected on their experiences at the Games, and talked about memories of watching the Olympics as kids.

They even swapped presents.

Snoop gifted Tucci a jacket featuring Tucci eating spaghetti with his name on it, while Tucci gave Snoop a white turtleneck sweater. Tucci also got an "Searching for Stanley Tucci" jacket, and at one point they stepped out together dressed like stylish twins.

In another NBC segment for his series "La Tucci Vita," Tucci visited Camparino and revealed why Campari should be the drink of choice for fans watching the Olympics. He explained that Campari, invented in Milan in 1915, is the perfect pre-meal aperitivo because it stimulates the appetite.

Throughout the Games, Tucci attended events including the opening ceremony, the pair skating free skating team event, and the figure skating pair skating short program, consistently layering for the cold while maintaining a sharp yet casual look.

But as polished as the promos were, some of the most unforgettable scenes came from the stands.

Jake Paul and Jutta Leerdam

When Dutch speedskater Jutta Leerdam delivered the defining race of her career on February 9, emotions exploded.

Leerdam roared to Olympic gold in the women's 1000m, setting a new Olympic record of 1:12.31 to lead a Dutch one-two finish and deliver the Netherlands' first medals of the Games.

She finished 0.28 seconds ahead of compatriot Femke Kok, who had briefly held the Olympic record with 1:12.59, while Japan's Miho Takagi took bronze.

Inside a packed 7,500-seat arena in Milan's western suburbs, most of the crowd wore Dutch orange. Among them was her fiancé, Jake Paul.

He stood in the second row, bawling his eyes out as she crossed the line. Leerdam herself was in tears as she celebrated afterward.

"I knew that if during the race I would feel tired, I wasn't allowed to feel tired," Leerdam said, according to The Guardian. "I told myself: 'You have 80 years to recover from this. You can feel tired after. You don't want to live with that regret. You fought so hard for this.'"

It was her first Olympic gold and second overall medal after silver in Beijing 2022. Paul and Leerdam had announced their engagement in March 2025 with a joint Instagram post.

But in Milan, their love was seen in real time.

And another sports power couple experienced a triumphant chapter of their own.

Myles Garrett and Chloe Kim

Chloe Kim aimed to become the first snowboarder to win three consecutive Olympic halfpipe gold medals. It was not meant to be.

At Livigno Snow Park, the 25-year-old American fell on each of her final two runs and settled for silver. South Korea's 17-year-old Choi Ga-on overtook her in the third round with a 90.25, while Kim's first-run score of 88.00 remained her best.

With boyfriend and NFL star Myles Garrett watching, Kim had opened strong with a switch double cork 1080. She previously won gold at 17 in PyeongChang 2018 and again in Beijing 2022.

Still, silver is meant to be celebrated.

After the event, Garrett surprised her with a custom pink Ford Bronco, which the couple shared on social media.

According to Sports Illustrated, the gift could land in the $100,000-plus range depending on custom work, while the Times of India reported automotive experts estimate the total value north of $115,000.

It was flashy, emotional, and completely on brand for the Olympics. And they were far from the only stars lighting up the venues.

More Stars in the Spotlight

Flavor Flav attended the women's monobob bobsleigh and later the skeleton mixed team event on February 15 at the Cortina Sliding Centre.

At some appearances, he was seen wearing a leather jacket with the Cane's logo, a hoodie topped with a pom, and flashy sunglasses as he celebrated from the stands.

Charlize Theron, a UN Peace Ambassador and South African actress, delivered a speech during the opening ceremony.

She wore a figure-hugging black dress with black stiletto sandals, her short blonde hair slicked back and accessorized with elegant diamond earrings and rings.

George and Amal Clooney were seen arriving at the airport on February 7 before attending the Omega House opening that night.

George wore a dark suit with a white button-down shirt and no tie, while Amal stunned in a nearly matching dark floor-length gown with black heels and drop earrings with her brown hair cascading down her back.

Usher arrived at Teatro Alla Scala for the opening ceremony wearing the Polo Ralph Lauren Team USA 2026 Shearling Jacket over a denim outfit with brown boots and dark glasses, giving off cowboy energy minus the hat.

Katherine LaNasa stepped onto the red carpet in a black and white patterned suit with her hair pulled back, blending elegance with edge.

Halle Bailey and Regé-Jean Page attended the women's single skating short program on February 17 at the Milano Ice Skating Arena. She wore a bold white shaggy faux-fur coat with long wispy fibers, sheer pantyhose, white stilettos, and a white outfit with short shorts underneath.

Page chose a layered neutral look featuring a cream utility-style jacket with a black collar over a tan turtleneck and dark trousers.

Martha Stewart also appeared at the figure skating women single skating short program, wearing a dark USA team sweater while commenting for NBC alongside Snoop.

Jeff Goldblum arrived at the opening ceremony with his wife Emilie Livingston and their sons dressed in stylish yet relaxed ensembles. The family later attended the men's single skating event on February 13, again balancing elegance with a casual relaxed vibe.

As the Winter Olympics continue through February 22, Milano Cortina 2026 has already delivered far more than medals. It has given us tears in the second row, pink Broncos in the parking lot, couture on the red carpet, and one opening ceremony performance that still has people talking.

And if the photos coming out of Italy prove anything, it is that some of the most unforgettable Olympic moments are unfolding just a few seats away from the action, with plenty more still to come.