Everett Collection
August 24, 2015 03:55 PM

In 1990, both Charlie Sheen and Emilio Estevez were riding high in Hollywood. Sheen counted among his recent successes Major League and Wall Street, while Estevez had Stakeout. Producers hoped that the brothers’ combined marquee value would make Men at Work a success.

It was, and when the film hit theaters on Aug. 24, 1990, audiences overlooked so-so reviews and made the low-budget comedy a modest hit. The film, which Emilio also directed, has made $16 million to date, and long after its theatrical run, it made its way into homes via basic cable airings well through the mid-’90s. It also helped to better establish Emilio as a director; following Men at Work, he’d go on to direct both features and TV.

Men at Work is but one example of the long history of Sheen-Estevez family collaborations. That’s one of the fun things about growing up in a showbiz family – any project could be a potential family reunion, and the Sheen-Estevez actors have racked up quite a few.

Here, then, are all the movies and TV shows that have featured some combination of Charlie, Emilio, brother Ramon Estevez, sister Renée Estevez and their father, Martin Sheen.

Badlands (1973)

Only 33 and looking like a hunky combo of Charlie and Emilio, Martin plays a drifter who runs off with a teenage girl (Sissy Spacek), committing a cross-country crime spree. Badlands might remind you of a more naturalistic Natural Born Killers, and it’s one of Martin Sheen’s greatest roles.

It’s also notable for featuring Charlie and Emilio in their first onscreen roles – as “Boy Under Lamppost No. 1” and “Boy Under Lamppost No. 2,” respectively.

Apocalypse Now (1979)

Arguably Martin’s most-acclaimed starring role, the war epic features Charlie in an uncredited role as an extra.

The Dead Zone (1983)

Most famously, Martin plays a presidential hopeful who may just bring about a nuclear holocaust. (Clearly, things would fare better when he took the Oval Office in The West Wing.) Ramon Estevez shows up in a brief scene.

Charlie Sheen’s Changing Looks!

The Fourth Wise Man (1985)

This religious epic made-for-TV movie stars Martin but features Ramon, Charlie and even Martin’s brother Joe Estevez in bit roles.

Wisdom (1986)

Emilio’s first directorial effort had him acting opposite his St. Elmo’s Fire costar Demi Moore. And while Emilio may be the eldest of the siblings – he’s 53, while Charlie is 49 – Charlie puts on a major “big brother” vibe in his small role as Charlie’s boss.

Wall Street (1987)

Martin’s first major role opposite one of his children happened in the Oliver Stone classic, in which he plays the father to Charlie’s hotshot stockbroker character. In this scene, the elder Sheen reminds the younger Sheen that he’s lost his soul to the pursuit of money.

Young Guns (1988)

It could have been just “the Brat Pack brothers go Western,” but Young Guns proved to be a hit with audiences. The film, which ended up making $45 million, had Emilio starring as Billy the Kid and Charlie in a supporting role as the cowboy Dick Brewer. Emilio reprised his role in the 1990 sequel, Young Guns II, but Charlie did not, on account of having bitten the big one in a shoot-out midway through the first movie.

Cadence (1990)

In Martin’s sole directing credit, Charlie plays a soldier who goes AWOL and is punished by being placed in a military prison ruled by a cruel warden, played by Martin. The film also features Ramon in a supporting role.

Loaded Weapon 1 (1993)

In 1991, Charlie starred in Hot Shots!, a spoof of Top Gun. In 1993, Emilio starred in this National Lampoon spoof of the Lethal Weapon movies, and the fact that one brother followed in the other’s footsteps is referenced directly in the script, in one fourth-wall-breaking joke.

Charlie also has a cameo as a valet attendant.

The War at Home (1996)

(Warning: This clip contains NSFW language.) Emilio both directs and stars in this film about a Vietnam vet attempting to readjust to life at home after the war. Martin plays Emilio’s father opposite Kathy Bates, who plays his mother. Renée plays a supporting role.

No Code of Conduct (1998)

Martin and Charlie once again played father and son in this cop thriller, which is perhaps most notable for having been written by Charlie and directed by Bret Michaels, of all people. Renée and Joe both play small parts.

Rated X (2000)

Charlie and Emilio starred together in this Showtime original about the Mitchell brothers, real-life strip club owners and porn kings who co-directed the first feature-length hardcore porn film, Behind the Green Door, in 1972.

Spin City (2002)

Martin appeared in a single episode of the sixth season of the show, playing the con man father who abandoned Charlie’s character ages ago.

The West Wing (2003)

The fourth-season finale of the beloved political drama had Emilio playing a younger version of his father’s character, President Jed Bartlett, in an uncredited cameo. (And no, sadly, the above clip from that episode doesn’t show the cameo. It doesn’t seem to be available online – apologies.) From 1999 to 2006, Renée played Nancy, one of Bartlett’s secretaries on the show, while Ramon played a small role in a 2003 episode.

Two and a Half Men (2005)

Martin appeared in a single episode of Charlie’s sitcom, playing the father to the mentally unbalanced Rose (Melanie Lynskey), who’s none too happy to find out that Charlie has slept with Rose.

Bobby (2006)

A sprawling ensemble piece about the last few hours of Robert Kennedy’s life, Bobby starred everyone from Lindsay Lohan to Sharon Stone. The film was written and directed by Emilio, who once again plays opposite Demi Moore. Martin, meanwhile, plays a wealthy donor to Kennedy’s presidential campaign.

Two and a Half Men (2008)

In the sixth season of Sheen’s sitcom, Estevez guest-starred as an old buddy of Sheen’s whose reckless lifestyle causes him to die suddenly, prompting Sheen to re-evaluate the choices he’s made in his life. Draw your own conclusions about whether it had any effect on the way Sheen conducted himself in the next few years.

The Way (2010)

Emilio also wrote and directed this film, which stars Martin as a grieving father walking a Catholic pilgrimage route in Spain after his son (Emilio again) is killed in an accident while making the same journey. Renée plays a supporting role, while Ramon served as an executive producer.

Anger Management (2012)

Charlie had starred in two sitcoms previously, and Martin had appeared in a single episode of each. In Anger Management, Martin stepped up his game, playing Charlie’s onscreen father in 20 of the series’ 100 episodes. And yes, just like Charlie’s character, Martin’s role included some serious displays of anger as well. Ramon served as co-executive producer on 79 episodes of the show, while Renée wrote four episodes.

Honorable Mentions

• The TV films The Execution of Private Slovik (1974) and Out of the Darkness (1985) both star Martin and feature Charlie in bit roles.
• Joe plays a supporting role in the 1974 TV movie The California Kid, which starred Martin.
• The 1982 TV movie In the Custody of Strangers has Martin and Emilio playing father and son.
• Emilio’s 1985 movie That Was Then This Is Now has Ramon in a supporting role.
• The 1988 thriller A Letter from Death Row has Martin playing a supporting role and Charlie showing up in a brief role as a cop. In 1988, Martin and Charlie both appeared in Free Money, one of the final onscreen roles of Marlon Brando.
• The 1989 film Never on a Tuesday has Charlie making a cameo as a thief and Emilio as a tow truck driver.
• The 1989 TV movie Nightbreaker features Martin and Emilio playing older and younger versions of the same character.
• Ramon also plays a supporting role opposite Martin in the 1989 comedy Beverly Hills Brats.
• Renée plays a small role in Charlie’s 1993 film Deadfall, as well as in 2001’s Good Advice. Both Charlie and Renée appear in small roles in 1997’s Loose Women.
• Charlie’s 1997 thriller Shadow Conspiracy features Ramon in a supporting role.

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