Will Charlie Sheen's career ever recover?
No, it won’t.share
Charlie Sheen is finished as a drawing performer in Hollywood.
Besides the debacle that was his departure from the television series Two and a Half Men, his followup series Anger Management isn’t attracting significant interest in syndication and his film career has been dead for almost two decades. Basically he is in a career rut of his own making and from which it would be impossible for him climb out of even if there weren’t other issues.
His drug use/abuse - Charlie Sheen has had substance abuse problems for nearly 30 years. While he recently claimed that he had beaten his addictions (again) there’s simply no reason to believe him and so major productions aren’t going to take a chance doing so. Unlike Robert Downey Jr., Sheen was never a stellar performer in films or on television and so it’s unlikely that he would experience the career turnaround that Downey has.
His mental and emotional issues - Beyond his drug abuse, it’s clear that Charlie Sheen has one or more issues with mental illness. While that’s treatable and he seems to be able to moderate his excesses on occasion, it’s just too risky to use him when you cannot be certain that he’ll be able to “maintain” long enough to complete your project. While he might be good in cameo roles, anything beyond that is a risk and he’s not a big enough box office draw to make it an acceptable.
His health - Since Sheen came out and admitted that he had contracted HIV/AIDS (Which considering what it’s cost him was a surprisingly brave thing to do) it’s likely that many productions which may have considered using him have factored that into the equation and decided to look for another performer. While there are probably multiple actors who are suffering from the same chronic illness, most of them don’t come with Sheen’s other baggage. His roles going forward would have to be careful chosen; and it’s unlikely that he would be capable of traveling to location shoots where endemic illnesses are a common problem.
So no, questioner, Charlie Sheen will never again be an actor of any consequence in Hollywood.
However, if media report are true, then Charlie Sheen will be able to “manage” for the remainder of his life, even if he doesn’t find any other acting roles. Despite selling his profit participation in Two and a Half Men, Sheen still apparently owns his rights from Anger Management. He’s rumored to earn at least $500k per month in royalties, which is more than enough for the majority of people to maintain a decent lifestyle.