Charlie Sheen isn’t the most likely candidate to host a charity toy drive for kids. The whole prostitutes-crack-tiger-blood era of the famously troubled star didn’t exactly radiate holiday cheer. But the actor born Carlos Irwin Estévez has been on a redemption tour of late, which kicked off in September with a two-part Netflix documentary, aka Charlie Sheen, and a memoir, The Book of Sheen, both of which he’s spent the fall promoting.
So there he was on Instagram, plugging his upcoming appearance.
“I’m inviting you to join me on December 2 at the Stella Jets hangar in Dallas, Texas for the Doing Good in Dallas charity ball,” he said, looking younger than his 60 years, if a bit twitchy. “This amazing event helps raise much-needed funds to support children in need this holiday season. And I would love for you to be a part of it.”
How could I not be curious? Once an “icon of decadence,” as his Two and a Half Men co-star Jon Cryer described him in the recent documentary, Sheen had become jolly St. Nick.
News Roundups
On a chilly Tuesday night, I rolled up to the Addison headquarters for Stella Jets, a fleet of luxury chartered planes owned by Tia Minzoni, who bought the airline from a Detroit company and moved it to North Texas a few years ago. I had one question: Why Charlie Sheen?
“We’re doing some Stella experiences with him in 2026,” Minzoni explained to me, when I met her before the gala began, “so this just made sense.”
It also worked. The event sold out. A few weeks ago, I’d never heard of Stella Jets, and now I was covering their inaugural charity bash, the latest stop on the Charlie Sheen redemption tour.
Rapper Twista (from left), singer-songwriter Mario, Stella Jets CEO Tia Minzoni, ballroom dancer Sharna Burgess, actor Brian Austin Green, actor Charlie Sheen and emcee Lady Jade pose on the red carpet during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
Dallas Cowboys, Twista, ‘Beverly Hills, 90210′
The Stella Jets airplane hangar had been decorated in a way that reminded me of those fantasy dates on The Bachelor: dancing lights, couches beside fire pits, red roses on round tables — but with planes.
It was 43 degrees outside and not much warmer in the cavernous space, dotted with pyramid patio heaters, as Dallas Cowboys players made their way down a red carpet. Rolling with the aviation theme, I asked the best or worst thing that ever happened to them on a flight.
“I was visiting my brother in New York, and the wheels fell off when we landed,” said Cowboys safety Juanyeh Thomas, in a dapper beret and chunky black glasses. Thomas’ brother Azareye’h Thomas plays for the New York Jets, but as a nervous flyer, I was more interested in how he knew this catastrophe had taken place. “I heard the pop!” he said. “Man, it was crazy.”
Dallas Cowboys safety Juanyeh Thomas poses on the red carpet during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
Defensive end Earnest Brown IV flew to Hawaii next to a crying baby. Offensive tackle Dakoda Shepley got spooked by a failed approach into Cuba. It was endearing to learn these gladiators suffered like the rest of us, strapped in a tin can in the sky where their superpowers were useless.
The evening’s theme was the ’90s, though at some point that changed to the ’90s and ’00s. DJ Astronaut spun tunes from ’N Sync and Tupac and Gwen Stefani as more boldface names made their appearances. Actor Jason Mitchell, who played Eazy-E in Straight Outta Compton, was followed by Brian Austin Green from Beverly Hills, 90210, and seeing his familiar face at the end of the red carpet — David Silver, OMG — actually made me gasp. He cozied up to his fiancée, Dancing with the Stars’ Sharna Burgess, as the cameras clicked.
Everyone had wretched stories about flying. Vomiting passengers, near-collisions, bad odors. The answers turned out to be a pretty decent plug for chartering your own private jet.
Rapper Twista performs during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
“I had an anxiety attack on a plane once,” said the rapper Twista, one of the evening’s performers. Twista hit No. 1 in 2004 with “Slow Jamz,” a collaboration with Kanye West and Jamie Foxx, and later in the evening, he’d get the audience on their feet with a rousing rendition of that song. For now, though, he was just a fellow nervous flyer.
“Does flying make you anxious?” I asked.
“I hate it,” he said.
“Me too,” I said, and he gave me a fist bump.
‘Eye of the Tiger’
It was shortly after 8:30 p.m. when the gala got cranking. Lady Jade, a stylish and dynamic former radio host on K104 (KKDA-FM), would be handling most of the evening’s duties as co-host. Sheen took the stage to the opening power chords of “Eye of the Tiger.”
That was a subtle “tiger blood” reference (nice one, DJ Astronaut) and the only nod to a bizarre stretch of time when Sheen seemed almost determined to implode in plain sight. He once told 20/20, “I have a different brain, I have a different heart. I’ve got tiger blood,” a line that went instantly viral.
Now he looked clean-cut in a blue blazer and white button-down, far removed from the sleep-deprived tornado who filled venues in 2011 with an improvisational stage show called “My Violent Torpedo of Truth/Defeat Is Not an Option.” He looked respectable, maybe even a bit shy.
Actor Charlie Sheen greets attendees during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
“It’s an honor to be here,” he said, squinting a bit in the spotlight. “What I would hope from all of you is that you showed up in a generous mood, because it is the season of giving, and we’re gonna ask that you play loose and fast with your wallets and checkbooks.”
This didn’t strike me as a laugh line, but the silence in the audience seemed to spook Sheen, who perhaps anticipated cheering. “That didn’t get any kind of response at all,” he said sarcastically, going off-script to poke fun at himself, which did get a laugh. “Everybody’s like, s—, left [my wallet] in the car.”
The peak of Sheen’s fame was playing a wisecracker on Two and a Half Men, and the lowest point of his downfall was being a man so substance-addled he’d say anything. “I’ve got poetry in my fingertips,” he once rattled off to Alex Jones during a radio interview. “I’m an F-18, bro. And I will destroy you in the air.”
He had a different role now. Real-life human. Sober adult trying to make amends to his children (he has five) and the famous father who once fought for him publicly. In the few minutes of banter that opened the gala, he got a bit tongue-tied, and I noticed a stammer. Had he always had that? A Google search took me to “Charlie Sheen Reveals How Lifelong Struggle with Stuttering Led Him to Drink” on a website for the Stuttering Foundation. The story mentioned a recent conversation he’d had on Good Morning America, when he told Michael Strahan of booze, “It gave me freedom of speech.”
The Book of Sheen, which had been placed at each of the seats at the Addison gala, contained other tender admissions about his life. He’d had sex with men. He’d lost his virginity to a Las Vegas escort. The late-night punchlines that once feasted on his bad-boy behavior never talked about the lost boy inside, because that was hard to play for laughs.
Copies of Charlie Sheen’s memoir are seen on a table during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
So if he looked a little creaky up there, a bit out of his element, this was also a sign he was figuring out a new element, letting himself be seen. He was not an F-18, after all. More like a shaky Cessna trying to get off the ground.
He promised the audience he’d return at the end of the show to help auction a VIP experience. “That’s where you clap,” he deadpanned, and the audience obliged. It was a strange disconnect, like everyone wanted to love him, but we didn’t know how.
‘Does anybody care?’
Singer-songwriter Mario performs during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
The next hour was a fast-paced series of crowd-pleasing sets. Violinist Richmond Punch tore it up with Michael Jackson’s “Don’t Stop ‘Til You Get Enough.” R&B singer Mario crooned his 2004 hit, “Let Me Love You.” By the time Twista came out, the millennials were deep enough in their cocktails to unself-consciously rap along.
Charlie Sheen did return. It was at the tail end of a live auction spearheaded by a guy in a cowboy hat who spoke in that hebbeda-hebbeda voice of rodeos.
Sheen addressed the audience, who had reached the chatty hour. “I’m in the middle of a promotional tour for a book that’s been sitting in the middle of your table most of the night, and I hope you’ll enjoy it,” he said, but the echoey hangar made it hard to hear. “So I have an appearance,” he began, then stopped. “Does anybody care?”
The audience, once too quiet, was now too loud. Yes, we care! He explained his appearance was in Sacramento, where he was flying the next day, and the final auction item would be accompanying him on that trip, staying at the Hard Rock, a VIP experience that had already been receiving online bids and whose current top bid was $20,000.
“I’m going to enlist the help of this gentleman,” he said, pointing to the auctioneer. “But can you do it at, like, half that speed? Slow it down?”
Actor and host Charlie Sheen starts the bidding for a one day trip to Sacramento with him on a private jet during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
If I had to read Sheen’s mind at that moment, he was anxious nobody would bid that high. Or maybe that’s projection, because I was definitely worried nobody would bid that high. Who drops $20,000 on a whim to fly to Sacramento with Charlie Sheen — tomorrow? The only high roller I knew in this room likely to blow that kind of dough was, well, Charlie Sheen.
The auctioneer slowed his roll, and the bids started coming. Twenty-five, 26. The crowd got into this. Thirty, 31. Sheen let out an exclamation of pleasure each time we reached a higher number. Nicely done, there it is. We were crawling through the mid-30s when someone yelled, “It’s for the kids!”
A reminder, in case we needed one. This evening was not about the return of a troubled celebrity, nor open bars or Instagram experiences or meeting a hot Dallas Cowboy, though each of those was available.
“It’s for the kids,” Sheen repeated. The money raised would fund a Christmas celebration for about 2,000 children. With that, a guy in the audience bid $40,000. Sold!
His name was Kevin Mei. “What I like is to give back for the kids,” he told me, after I pushed past the high fives and hugs that greeted him. “It’s the greatest investment.”
Kevin Mei reacts after placing the winning bid for a day trip with actor Charlie Sheen on a private jet during the Doing Good in Dallas gala at Stella Jets, Tuesday, Dec. 2, 2025, in Addison.
Elías Valverde II / Staff Photographer
The crowd started exiting the chilly hangar, returning to their warm hearths. “Doing Good in Dallas” had come to an end. But I like to think that one day, in a not-so-distant future, kids in North Texas will tear open the glittering wrapper of their presents, smile at what Santa brought them, and the adults might flash that knowing smile, because who would have thought? This year, Santa was Charlie Sheen.