Charlie Sheen is attempting to make a comeback with Ramble On. The controversial Emmy-nominated actor has been rather absent from the industry in recent years. His last movie credit came from the poorly received 9/11 in 2017. He has also been illusive in the TV realm, last appearing as himself in an uncredited role in How to Be a Bookie.
After being fired from Two and a Half Men in 2011, Sheen has shown no signs of wanting to return to forefront until the trailer landed for Ramble On. From Entourage writer/creator Doug Ellin, the show is described as a comedy drama that will focus on established stars who are looking to reinvent their careers, and also aspiring performers seeking to make their own name in an ever-growing competitive environment. As of yet, the series is still in post-production and finer details are somewhat sparse. However, there is plenty to be dissected. Here’s everything we know.
What the Trailer for Ramble On Tells Us
The first thing to point out in the Ramble On trailer is that it is stacked full of talent. Joining Sheen are the likes of Kevin Dillon (Entourage), Kevin Connolly (Entourage), Jamie-Lynn Sigler (The Sopranos), John C. McGinley (Scrubs), Larry Joe Campbell (The King of Queens), and Martin Sheen (Apocalypse Now). The show is set around the inner-workings of a podcast. With their backers, including Mark Cuban, on the point of cancelling, the trailer follows Kevin Connolly and Kevin Dillon as podcast producers frantically trying to come up with a new hit after their $500,000 project starts to fail. In a last-ditch attempt, they ask Charlie Sheen to join the podcast, only to find that he is just as desperate as they are, or maybe more so.
Kevin Dillon, Kevin Connolly, and Charlie Sheen are playing themselves in the show. Leveraging Sheen’s somewhat tarnished public profile, it seems the show will see him portray an exaggerated version of himself, as he discloses he has nothing left; no money, no offers, and no love. As of yet, it is unknown which actors will be playing themselves and which will be playing fictional characters. However, Martin Sheen (Charlie’s real-life father) is seen having a fatherly walk-and-talk with Charlie in the trailer, so, chances are he will be playing himself. Other cast members include Ana Ortiz, Bre-Z, Julissa Calderon, and Sara Sanderson.
When Will Ramble On Be Released?
The release of the Ramble On trailer is an unconventional one. This is because, as of writing, the series does not have a home or a release date. Typically, a series will drop its trailer when it has a release date set in stone and a network provider fully on board. However, Doug Ellin has taken on a different approach and has released the trailer himself as a means to shop the idea around Hollywood. The trailer was initially revealed on Victory The Podcast. The series also has its own website TheRambleOnProject.com where the trailer can be watched in full and visitors are treated to behind the scenes content. However, this bold move isn’t new territory for Ellin.
After his movie Kissing a Fool flopped at the box office, Ellin became unemployable. He was thinking of giving up on his dream and going to law school until Mark Wahlberg pitched him the idea for Entourage. From here, he hustled his way to success and Entourage ran for 8 seasons, winning 6 Primetime Emmys. It also spawned a feature length movie in 2015. So, with such a triumph under his belt, why is Ellin now having to hustle around tinseltown again?
Ramble On is believed to be keeping all opportunities open for discussion, whether that be a major television network or streaming provider. Entourage originally aired on HBO, so this series could easily follow suit and find an audience there. Yet, it seems the problem may lie with the casting of Charlie Sheen.
Is Charlie Sheen Still a Bankable Star?
On December 25, 2009, Sheen was arrested for allegedly assaulting his wife at the time, Brooke Mueller. He was booked on suspicion of second-degree assault, menacing and criminal mischief. He was released the same day from jail after posting an $8,500 bond. Prior to this, the actor had been known to have a problem with substance abuse, eventually suffering a stroke after overdosing while using cocaine. As of 2025, he is now clean and sober.
Sheen’s stint on Two and a Half Men saw him become one of the highest-paid TV actors of all time. His character, although fictional and named Charlie Harper, cheekily played into his public image as a loose canon. In turn, the show helped boost his public profile. However, Sheen was eventually canned from the show and replaced by Ashton Kutcher after a falling out behind the scenes eventually went public. Sheen was let go from the show after he made a string of negative comments about series creator Chuck Lorre. Couple this with further personal scandals following his departure and it just might be that the big wigs of Hollywood are reluctant to give Ramble On a home. It is unclear if the entire season has been filmed, as Ellin is currently only showing the pilot episode around Hollywood.
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