Charlie Sheen’s ‘Ramble On’ Cast & Character Guide

Although an official release date is unknown, the new trailer for Ramble On has Entourage fans eagerly anticipating the new year. Created by Doug Ellin, the spiritual successor follows several Hollywood stars who’ve passed their prime and fallen on hard times. The main draw is Charlie Sheen, who portrays a heightened version of himself as he tries to recapture past glory and rekindle his acting career.

Along with Sheen, several Entourage actors play themselves in the upcoming series, including Kevin Connolly and Kevin Dillon, who famously portrayed Eric Murphy and Johnny “Drama” Chase on the hit HBO drama. As Ellin attempts to sell the pilot episode to willing networks or streamers, it’s time to meet who will take center stage in the new series about finding second chances in Hollywood.

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Charlie Sheen

Charlie Sheen toys with his public bad-boy image in Ramble On, playing a semi-fictional version of himself. Strapped for cash and having few career prospects left, Sheen is asked to star in a popular podcast to reignite his fortune and fame. Reluctant at first, Sheen desperately agrees after soliciting advice from his equally famous father, Martin Sheen. Whether poking fun at his age or the depth of his lavish swimming pool, Sheen gives a deprecating, self-aware performance.

Charlie Sheen is “the highest-paid male TV actor of all time,” according to the Ramble On trailer, earning such a feat by starring in Two and a Half Men from 2003 to 2011 and Anger Management from 2012 to 2014. Before television, Sheen’s best movie performances include Platoon, Wall Street, Lucas, Major League, Eight Men Out, Young Guns, and Hot Shots!

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Martin Sheen

Martin Sheen plays himself in Ramble On, expressing concern for his son Charlie’s public image. In the trailer, Charlie asks his father’s advice about joining the podcast. Martin warns that his son must be prepared for intense media scrutiny after years of courting controversy for his untoward behavior. Martin and Charlie have plenty of experience working together, dating to Wall Street for director Oliver Stone.

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A tremendous actor with multiple Emmy and Golden Globe Awards to his name, Martin Sheen has starred in titanic movie classics like Terrence Malik’s Bad Lands, Francis Ford Coppola’s Apocalypse Now, Richard Attenborough’s Gandhi, Oliver Stone’s Wall Street and JFK, Steven Spielberg’s Catch Me if You Can, Martin Scorsese’s The Departed, and more. Equally accomplished on TV, Sheen is best known for his work on The West Wing as well as Grace and Frankie.

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Kevin Connolly

Kevin Connolly plays himself in Ramble On, serving as the brainchild behind the podcast seeking Charlie Sheen’s star power. The trailer reveals that Connolly cannot get a line of credit from the bank despite investing $500,000 in the podcast already. As such, Connolly solicits Charlie Sheen’s buzzy presence on the show, arriving at Sheen’s Hollywood mansion to hash out a deal.

Connolly famously played Hollywood talent agent Eric Murphy in Entourage, tasked with ensuring that his best friend and main client, Vincent Chase (Adrian Grenier), stays employed and steadily climbs atop Hollywood’s A-list. Watching the trailer, it’s difficult to separate Connolly from Eric Murphy, suggesting that Ramble On is a thinly veiled Entourage reboot. Connolly has also starred in The Notebook, Secretariat, Antwone Fisher, and Unhappily Ever After.

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Kevin Dillon

Rounding out the Entourage reunion, Kevin Dillon plays himself in Ramble On. Along with Connolly, Dillon is a key podcaster seeking to hire Charlie Sheen to boost ratings. However, when Connolly mentions hiring Charlie, Dillon has little faith, saying, “You’re reaching if you think Charlie Sheen will do a podcast.” Having co-starred with Sheen in Platoon nearly 40 years ago, Dillon would know.

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The younger brother of Matt Dillon, Kevin Dillon’s most notable credits include The Blob, The Doors, Blue Bloods, That’s Life, How to be a Gentleman, Poseidon, Hotel for Dogs, On the Line, Mob Land, and Reagan. In 2020, he and Kevin Connolly launched Victory the Podcast with Entourage creator Doug Ellin, which many attribute to the creation of Ramble On.

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Jamie-Lynn Sigler

Jamie-Lynn Sigler plays a heightened version of herself in Ramble On, keeping with the meta, self-reflexive show motif. The trailer reveals Kevin Dillon appearing at Jamie-Lynn’s podcast studio to ask for advice. With Kevin unaware of her topical discussions, Jamie-Lynn says her podcast is about “postpartum depression, crowning, nipple chafing,” and other motherhood realities that immediately sober Kevin.

Although Sigler will always be known for playing Meadow Soprano on the hit HBO mob drama The Sopranos, other credits include Big Sky, Guys with Kids, Beef House, Baby Daddy, Ugly Betty, and more. Sigler also guest starred as herself on Entourage, becoming romantically involved with Turtle (Jerry Ferrara). Sigler also has a podcast with her Sopranos sibling, Robert Iler, called Not Today, Pal.

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Zulay Henao

Colombian-American actor Zulay Henao stars as an unknown character in Ramble On. In the trailer, it’s clear that Henao’s character is romantically involved with Kevin Connolly and is a partial investor in the podcast that the series centers on. When Kevin tells his partner they need more money, Henao says, “Why do we have to put more money in? I’m scared.” This sets up a domestic quarrel that could put their relationship in jeopardy.

With a 20-year resume, Henao’s notable credits include If Loving You is Wrong, Love Thy Neighbor, The Oath, Stumptown, Snatched, Dashing Through the Snow, Takers, Meet the Blacks, Grand Isle, The House Next Door: Meet the Blacks 2, The Single Moms Club, Hostel: Part III, and more. Along with Henao, it’ll be interesting to see which lower-profile actors play fictional characters rather than versions of themselves in Ramble On.

As Ellin continues to shop Ramble On to distributors, it’s worth noting that John McGinley (Platoon, Scrubs), Mark Cuban (Shark Tank), Sara Sanderson (Uglies), and Emmanuelle Chriqui (Entourage) will also appear as themselves on the show. While their roles are unknown, additional cast members include Kimiko Glenn (Orange is the New Black), Ana Ortiz (Ugly Betty), and Bre-Z (All American).