Matt Rife shares his take on how he nabbed Macaulay Culkin and Charlie Sheen for his Christmas special's promo

The holiday season is busy for comedians, but few are making as much noise as Matt Rife, who launched his new Netflix project Matt Rife: Unwrapped — A Christmas Crowd Work Special on December 2. Directed by longtime friend and fellow comic Erik Griffin, the special captures Rife in Santa pants onstage in Phoenix, riffing on holiday traditions, awkward gift-giving moments, and a steady stream of NSFW crowd exchanges. But to hype the special’s release, Rife pulled off something most comics could never dream of: convincing Macaulay Culkin and Charlie Sheen to appear together in a surprise promo.

The Home Alone icon and the once-infamous “reformed bad boy of Netflix” had never even met before, yet Rife brought them into the same room for one chaotic, earnest, Christmas-themed shoot. In his interview with The Hollywood Reporter, Rife broke down exactly how the unexpected pairing came together, why he felt bold enough to ask, and how a four-and-a-half-hour lunch with Sheen led to one of the most surprising holiday promos of 2025.

How Matt Rife managed to land Macaulay Culkin and Charlie Sheen

In his interview with The Hollywood Reporter, Rife explained how he came up with the entire idea trying to find a festive angle that didn’t feel was tried before.

“Oh, man. I was trying to figure out how to promote the Christmas special, and when it comes to Christmas, you either think about Mariah Carey, Will Ferrell or Home Alone, right?” he explained. 

The challenge was that he had never met Culkin. Still, he asked his team to find a way to reach him. By some miracle, they did. Culkin’s agents sent him the pitch, and to Rife’s surprise, he immediately agreed: 

“They gave me his number and I called him up, told him the idea and he f*cking loved it. He was all about having some fun with it.”

With Culkin set, the second half of the equation came from pure coincidence. Out of nowhere, Charlie Sheen started following Rife on Instagram. Rife messaged him, directly, and without overthinking it. Sheen responded in kind, telling Rife he enjoyed his comedy and suggesting they grab lunch when Rife was next in L.A.

That timing could not have been better. Rife was already scheduled to shoot the promo the following week. So, he shot his shot again: 

“I texted Charlie and apologized if it was too forward since we hadn’t even met yet and he should feel free to say no, but I happened to be filming this promo for my new Christmas special and would he have any interest in doing it.” 

Rife sent the script. Sheen “loved it.” The two met for a marathon lunch lasting four and a half hours. Rife remembers it as the moment they clicked: 

“We just kind of fed off each other and got to know each other. It became a really, really friendly bunch.” 

The next day, Sheen arrived on set ready to work. Culkin came in with the same energy. Rife watched the pair, who had never crossed paths in their careers, interact like old friends. The level of professionalism impressed him most: 

“When Charlie arrived to set, he’s such a cool guy, very humble and soft spoken but the moment we called ‘action’ on the very first shot, you can see the switch flip in his head.” He added, “That’s just who they both are, and why they are the absolute best.”

Rife’s friend on set joked that he might be the only person on Earth that could bring Macaulay and Charlie Sheen together. Rife admits it felt that way. The lunch with Sheen was its own adventure. Rife said they talked about everything from early-career stories to ghosts, the paranormal, and even Rife’s unusual new purchase, Ed and Lorraine Warren’s former home and occult museum. Sheen explained how he discovered Rife in the first place: 

“Dude, I went down a rabbit hole watching all your specials and Instagram clips and you’re really talented.” 

Rife responded in typical Rife fashion: 

“That’s f*cking cool, I’m a fan of everything you’ve done, drugs included.”

By the time they wrapped filming, the promo felt less like studio marketing and more like a strange but charming Christmas miracle.

Everything we know about Rife’s Christmas special 

While the promo became the headline, Matt Rife: Unwrapped — A Christmas Crowd Work Special stands on its own as the comedian’s latest crowd-work entry. Rife describes crowd work as the most fun he can have onstage, even though it’s only a fraction of his longer shows. What makes this special different is its theme. Instead of open-ended improvisation, Rife steers the conversations toward shared holiday experiences, family chaos, gift-giving disasters, weird traditions, sex-related confessions, and the occasional bit of magic.

Some of the special’s most talked-about interactions involve surprising levels of honesty. One couple openly discussed their yearly calendar photos. Another audience member revealed his holiday-season pleas to avoid being in trouble. Rife even encountered a young magician named Gino who delivered card tricks mid-show. 

Beyond stand-up, Rife is expanding into acting. He appears next year in The Altruists opposite Julia Garner and Anthony Boyle, playing trader Ryan Saleme. He’s also writing The Chasm, a climbing mockumentary, with Dan Lagana, who introduced him to Sheen.

Between his arena tour, film roles, and writing projects, Rife says he’s most proud simply of growth: selling out Madison Square Garden twice, landing roles he never thought he’d get, and giving back through his annual toy drive for Hasbro Children’s Hospital.

Matt Rife: Unwrapped — A Christmas Crowd Work Special is now available to stream on Netflix exclusively.