Two and a Half Men Turns 20: A Look Back at the Malibu Beach House’s Most Famous Guests — How Many Do You Remember?

MARTIN SHEEN & EMILIO ESTEVEZ

Charlie’s real-life dad played Rose’s father (Season 3, Episode 7), while older brother Emilio dropped by as an old drinking buddy who croaked on Charlie’s deck (Season 6, Episode 11).

DENISE RICHARDS & MILA KUNIS

Sheen’s then-wife and Kutcher’s current wife both put in appearances. Richards recurred as Charlie’s ex-girlfriend Lisa (Season 1, Episode 10); Kunis played free-spirit Vivian (Season 11, Episode 19).

ALLISON JANNEY & JAIME PRESSLY

Before Mom, Janney guest-starred as Alan’s online date Beverly (Season 4, Episode 15). Six years later, Pressly recurred as Jake’s much older girlfriend Tammy (Season 10, Episode 15).

MILEY CYRUS & EMILY OSMENT

Cyrus recurred as Jake’s love interest Missy (Season 10, Episode 4). Former Hannah Montana BFF-turned-Young Sheldon star Osment played Tammy’s daughter Ashley (Season 10, Episode 20).

HILARY DUFF

The fellow Disney Channel grad guest-starred as Walden’s Instagram-obsessed date Stacey (Season 10, Episode 23).

MARILU HENNER & CAROL KANE

Henner guest-starred as Stacey’s grandmother Linda (Season 10, Episode 23), while her Taxi costar played Melissa’s mom Shelly (Season 6, Episode 12).

ANNIE POTTS

Before she was Young Sheldon‘s Meemaw, the Designing Women vet played Judith’s alcoholic mother Lenore (Season 7, Episode 3).

KATY MIXON

Before she was cast as Melissa McCarthy’s TV sister on Mike & Molly, the future American Housewife star recurred as stripper/part-time masseuse Betsy (Season 7, Episode 16).

TERI HATCHER & LYNDA CARTER

The former Lois Lane guest-starred as Judith’s sister Liz (Season 1, Episode 19), while the OG Wonder Woman played herself… and had a threesome with Charlie’s daughter Jenny and Walden’s mother Robin (Season 11, Episode 6).

JENNA ELFMAN & THOMAS GIBSON

Elfman initially played Frankie, Alan’s first love interest following his divorce from Judith (Season 1, Episode 15). Eight years later, she returned as Dharma, opposite Gibson’s Greg, who were prospective buyers of Charlie’s Malibu beach house (Season 9, Episode 1).

PAGET BREWSTER

Before she joined Criminal Minds, Gibson’s longtime costar guest-starred as Alan’s high-school classmate Jamie Eckleberry (Season 2, Episode 12).

CHRIS O'DONNELL

Seven years before joining NCIS: Los Angeles, O’Donnell appeared as Charlie’s ex-girlfriend Jill—err, Bill (Season 1, Episode 18).

HEATHER LOCKLEAR & RICHARD KIND

The CBS comedy hosted a pair of Spin City reunions, with Locklear showing up as Alan’s divorce attorney (Season 1, Episode 21) and Kind showing up as Charlie’s agent Artie (Season 5, Episode 8).

ROBERT WAGNER & JENNY MCCARTHY

Wagner initially recurred as Evelyn’s beau Teddy (Season 4, Episode 24), while McCarthy initially played his daughter Courtney (Season 5, Episode 9). But during a crossover with CSI — yes, there was a crossover with CSI — it was revealed that Teddy and Courtney were grifters Nathan Krunk and Sylvia Fishman.

KEVIN SORBO & LUCY LAWLESS

TV’s Hercules played Kandi’s dad Andy (Season 3, Episode 20), while the erstwhile (and superior) Xena: Warrior Princess guest-starred as Pamela, the wife of a closeted ad exec (Season 2, Episode 18).

MEGAN FOX, CAMRYN MANHEIM & SARA RUE

Fox played Berta’s granddaughter Prudence (Season 1, Episode 12); Manheim played Berta’s sister Daisy (Season 2, Episode 7); and Rue played Berta’s daughter Naomi (Season 4, Episode 7).

YVETTE NICOLE BROWN & KEN JEONG

Prior to Community, Brown appeared as Mandy, an attendee at Judith’s women’s support group (Season 1, Episode 23). The following year, Jeong had a non-speaking role as “Male Nurse” (Season 2, Episode 17).

SEAN PENN, ELVIS COSTELLO & HARRY DEAN STANTON

Penn, Costello and Stanton cameoed as members of an exclusive men’s support group hosted by Charlie (Season 2, Episode 1).

JAMES EARL JONES

Three years before Alan gave the eulogy at Charlie’s funeral, Jones gave the eulogy when Charlie dreamt of his eventual demise (Season 6, Episode 11).

JEFF PROBST

The Survivor host revealed his bacon bits (Season 11, Episode 7), then returned for a swingers’ party. (Season 11 was wild, you guys.)

MARION ROSS

Happy Days’ Mrs. C turned up at the same swingers’ party as Probst and courted a down-on-his-luck Zippy (Season 11, Episode 12).

JENNIFER TAYLOR, JUDY GREER & BROOKE D'ORSAY

Six years before she was cast as Charlie’s fiancée Chelsea, Taylor guest-starred as Suzanne, a woman who takes an interest in Charlie while he’s out grocery shopping with Jake (Season 1, Episode 1).

Five years before she made her debut as Walden’s ex-wife Bridget, Greer guest-starred as Herb’s sister Myra (Season 4, Episode 19).

Six years before she was introduced as Walden’s girlfriend Kate, D’Orsay appeared as Robin, a younger woman with an even stronger libido than Charlie (Season 4, Episode 16).

STACEY KEACH & JOHN AMOS

Keach recurred as Chelsea’s father Tom (Season 7, Episode 13), while Amos played Tom’s long-lost love Ed (Season 7, Episode 16).

TRICIA HELFER

The Battlestar Galactica fave played Chelsea’s heartbroken college roommate Gail (Season 7, Episode 8). Would you be surprised to learn that Charlie eventually slept with her?

JOHN STAMOS

Stamos appeared in Kutcher’s first and last episodes. In his first appearance, he backed out of buying the Malibu beach house once he remembered that he and Charlie had a devil’s threeway there (Season 9, Episode 1). Then in the series finale, it was revealed that Stamos was hooking up with Bridget.

KATHY BATES

Before she recurred on Mike & Molly or headlined Chuck Lorre stoner comedy Disjointed, the Academy Award winner appeared to Alan in a dream as the spirit of his (allegedly) dead brother Charlie (Season 9, Episode 22). The part earned her an Emmy for Outstanding Guest Actress in a Comedy Series.

MICHAEL BOLTON

When a man loves a woman, he calls Michael Bolton, who first serenaded Zoey during Walden’s fireworks-laden marriage proposal (Season 10, Episode 1). Two years later, he sang at Walden and Alan’s wedding — yes, Walden and Alan’s wedding. A lot of stuff happened after all you Sheen fanatics stopped watching!

MICHAEL CLARKE DUNCAN

The Green Mile star played Jerome, a single father who came a-knockin’ when Jake took an interest in his daughter (Season 6, Episode 9). We’re still not sure how Sheen and Duncan maintained their composure during this scene.

STEVEN TYLER

Tyler lent his voice in Season 1, but didn’t appear on screen for another three years. Charlie had the gall to tell the Aerosmith frontman to pipe down, which resulted in a serious ass-whooping from his next-door neighbor (Season 4, Episode 2).

ENRIQUE IGLESIAS

You can run, you can hide but you can’t escape the Latin singer’s guest turn as a handsome repairman who steals Charlie’s Girlfriend of the Week (Season 4, Episode 23).

EDDIE VAN HALEN

Leave it to a rock-and-roll God to wander out of a men’s room and absolutely shred — which is precisely what Van Halen did during right before Charlie’s eyes (Season 7, Episode 1).

ZZ TOP

The legendary rock band guided Charlie on a trip through girlfriends’ past (Season 7, Episode 21).

BROOKE SHIELDS

The Suddenly Susan star played Danielle, a new neighbor who Charlie instantly regretted setting up with Alan (Season 4, Episode 14).

JASON ALEXANDER

The Seinfeld star, sporting a ludicrous toupee, scrubbed in for Two and a Half Men’s 200^th episode as Alan’s cardiologist, Dr. Goodman (Season 9, Episode 23).

CLORIS LEACHMAN

The Phyllis and Facts of Life star played Norma, an elderly next-door neighbor Alan bedded in hopes of gaining access to her fortune (Season 3, Episode 9). Suffice it to say, it didn’t work out.

GEORGIA ENGEL

The Mary Tyler Moore alum appeared as Lyndsey’s mother, who for a brief time was also Evelyn’s lover (Season 9, Episode 19).

CARL REINER, STEVE LAWRENCE, TIM CONWAY & GARRY MARSHALL

Reiner recurred in Seasons 7 and 11 and Evelyn’s eventual husband Harry. Fellow Hollywood legends Lawrence, Conway and Marshall attended Harry’s bachelor party (Season 11, Episode 13).

GARY BUSEY

Busey played Alan’s roomie at a psychiatric hospital. Because of course he did (Season 9, Episode 9).

ARNOLD SCWARZENEGGER & CHRISTIAN SLATER

Schwarzenegger’s Lieutenant Wagner appeared in the highly meta series finale and urged Alan and Walden to “wrap things up.” That was followed by an even more absurd cameo by Slater, who was arrested/mistaken for a very-much-alive Charlie Harper (Season 12, Episode 16).

CHUCK LORRE

The series’ co-creator had the last laugh, crushing Charlie Harper to smithereens before getting crushed by a second baby grand piano as Two and a Half Men was put out of its misery came to a close (Season 12, Episode 16).

Who was your favorite Two and a Half Men guest star? Sound off in Comments.

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