Charlie Sheen Is Making Wild Return To TV To Play Himself Alongside Some Entourage Stars

Charlie Sheen may have been absent from the TV spotlight for some time, but his reputation through hits like Two and a Half Men still precedes him. That’s probably how he landed his latest gig, as he's about to help headline a potential series called Ramble On, alongside Entourage stars Kevin Connolly and Kevin Dillon. Together, these three men are about to play the roles they were born to play: themselves.

From the sound of things, this new project is going to occupy a realm very similar to that of the HBO dramedy series about the perils of fame and fortune. It makes total sense, as Entourage creator Doug Ellin is the creative mind behind Ramble On, according to initial reporting from Deadline. Since this is a dramedy about “Hollywood veterans looking to reinvent their voices alongside up and comers looking to establish their own,” you can pretty easily imagine Charlie Sheen poking fun at his days of odd, meme-worthy interviews, with at least one reference to tiger’s blood. 

Even the supporting cast of Ramble On is quite impressive, with a guest appearance from Emmanuelle Chriqui highlighted in the announcement. That's worth noting as Chriqui is working with some of her Entourage co-workers for the first time after wrapping the series with the 2015 follow-up movie. Chriqui is only the beginning of an impressive bench of supporting players in Ramble On. Among the other actors on board are The Sopranos' Jamie-Lynn Sigler, What We Do In The Shadows’ Harvey Guillén, and last, but not least, the legendary Martin Sheen.

Kevin Dillon, Kevin Connolly, and Emmanuelle Chriqui in Entourage: The Movie and Martin Sheen in Grace and Frankie, pictured side by side.

(Image credit: Warner Bros/Netflix)

While we’ll be able to see the elder Sheen in the final episodes of Netflix’s Grace and Frankie, which are set to premiere at some point this year, we don’t know when Ramble On will bring him back to our screens. For the moment, there’s only an independently funded pilot filmed for Ramble On, with talks beginning in order to find an official home for production, distribution, and broadcast. 

If a deal is made, it would be a huge win for both Charlie Sheen and Doug Ellin, as they’ve been out of action for some time. Sheen’s last steady TV gig ended back in 2014, with the end of FX’s series adaptation of Anger Management; whereas Ellin’s Entourage came to a close in 2011, with the feature film being his last credited project. More importantly, at least in Charlie Sheen’s case, Ramble On would mean an end to Sheen’s alleged four-year blacklisting in Hollywood.

At the moment, Ramble On is in early days, with only a pilot to its name and a cast and crew committed to spring into action. In the meantime, if you’re looking for the 2022 TV schedule, and the winter/spring season debuts we know are on the books, that information’s out in the open. 

Mike Reyes
Senior Movies Contributor

CinemaBlend's James Bond (expert). Also versed in Large Scale Aggressors, time travel, and Guillermo del Toro. He fights for The User.