Charlie Sheen's Twin Sons Bob And Max Have Seriously Transformed

Charlie Sheen's youngest children, Bob and Max Sheen, have undergone a transformation. The last two kids of Charlie's brood, twins Bob and Max were born to the actor and this then-wife Brooke Mueller in 2009. Charlie's rep announced the happy news to People. "They're doing great," Stan Rosenfield shared at the time (via UPI). "And Brooke's doing great." Charlie's rep added, "He's a family man — now he has three daughters and two sons. He's a wonderful father."

Back then, Charlie and Mueller were still happily married and on good terms, but it wouldn't be long before their union crumbled. By 2010, they had both initiated divorce proceedings, and years later, they were fighting over Charlie's five-figure child support payments. 

Sheen family skeletons, including Charlie's unexpected HIV announcement, Mueller's experience with substance use, and her possible ties to Matthew Perry's death, have further cast a shadow over their family. In fact, Charlie, who also indulged in substance use in the past, is now a single father. "I've mostly been raising my 14-year-old boys," he told People in 2023. "Their mom has been trying to figure some stuff out on her end, so she's not in the picture too much right now." Let's see how far Bob and Max have come since then.

In September 2011, Max and Bob Sheen were still in the toddler stage, and judging from this picture (above) of them with their dad, Charlie Sheen, they still had their red hair. They were also getting a head start on their partying phase, as they dined with Charlie on his birthday. Given that the toddler's days back then probably amounted to little more than naptime, snack time, and playtime, allow us to fill you in on their father's year.

You see, 2011 was a big year for Charlie, and when we say big, we mean terrible. Months earlier, the actor lost his very lucrative gig on "Two and a Half Men" after descending into a historic rant about his boss, Chuck Lorre. He also offered up some truly bonkers commentary, including his infamous "tiger blood" quote, which he eventually blamed on the use of testosterone cream. "I was doing way too much testosterone cream," Sheen shared in 2017 (via E! News). "It metabolizes into basically a roid rage."

Fortunately, it seems Charlie calmed down by year's end.

Okay, so 2011 was also a big year for Max and Bob Sheen. In October of that year, their mother Brooke Mueller dressed them up in some adorable firefighter gear to attend Dream Halloween California, a charitable initiative that helps support children living with AIDS. According to CBS News, tickets that year cost attendees between $250-$300. The publication also noted that the event was a celebrity magnet and included fun Halloween adjacent activities, such as trick-or-treating.

It's unknown whether or not Charlie Sheen decided to attend the charitable event, but it doesn't appear as if he was photographed that night. Still, he was obviously in the Halloween spirit. According to IrishCentral, Charlie decided to dress up for Halloween as a rich, famous, though sometimes troubled, star: himself. "sheenius Trick or Treat Cadre! Got my Halloween costume..." he tweeted alongside a since-deleted photo of a mask made in his likeness. "All set! (yeah... This really confused the kids!!)"

Halloween is obviously a big deal in the Sheen family, as the next entry in Bob and Max Sheen's transformation includes yet another Halloween stop. In October 2013, Charlie Sheen and his ex wife, Denise Richards, who stepped in to help raise the young boys as Brooke Mueller worked toward getting sober, treated the young children to a day out at the pumpkin patch, according to E! News. And though the twins didn't pop up in the photo for that particular outing, they'd get their shine again really soon.

In October 2015, Mueller, who was still in her children's life in some capacity, took to Instagram to document another trip to the pumpkin patch. As you can see above, the boys seemingly had a blast as they held pumpkins and also took some time to play on a bounce house, despite their family drama. "The Sheen boys getting their Halloween on at the pumpkin patch!" Mueller captioned the Instagram photo.

In August 2018, Charlie Sheen posted a rare photographic update of his youngest kids, Max and Bob Sheen. Taking to Instagram, the actor posted a photo of the brothers posing as they stood in the sun. In true twin fashion, they rocked super similar blue and white outfits — right down to their matching button-downs. Charlie also urged users to follow Bob's since-deleted Instagram account. "Please follow this young man, or his twin bro will be really upset!" he captioned the photo.

Roughly one year later, the twins were under the care of their grandparents while Brooke Mueller attempted to get clean, according to a source who spoke with People. "The twins are doing fine and are living with their grandparents during this period," they said at the time. "Brooke has been in a trauma center for the past few weeks and is doing very well." Fortunately, things seem to be looking up for them and their family these days.

Bob and Max Sheen have been through a great deal of adversity during their short lives and they're not even 18 yet! However, they're still very much normal teenagers according to their dad, Charlie Sheen. "You know, the time spent worshipping their devices..." Charlie shared during his 2023 People interview. "Although on the flip side, when they're doing that it gives me a little time to not be dragging them all over the city. But I also feel like the screens detract them from having other opportunities to expand their minds in other areas."

Like Charlie, Brooke Mueller is currently sober. "It's been hard," Mueller shared with People in September 2024. "And a lot of people at my level of addiction don't make it." She continued, "In fact, most people don't. I worked really hard. It has not been easy. I am sober. I do work a program. I do believe in the Twelve Steps."

Given that Bob and Max are just years away from leaving the nest, let's hope both their parents continue the hard work they've put into being around!