Long before she won an Emmy for her performance on Chuck Lorre’s underrated Mom, Janney swung by as Beverly in the Season 4 episode, “My Damn Stalker,” as a date of Alan’s who turned out to be even more desperate, and less desirable than Zippy.
Before signing on to Criminal Minds, Brewster stopped by the Harper household in Season 2 as an old classmate of Alan’s who grew up to be a beautiful woman… but upon her return into his life showed more interest in Charlie. As it turned out, she had both brothers fooled. (Watch clip.)
The Academy Award nominee made a quick cameo in the Season 9 episode, “Frodo’s Headshots,” as a patient in the psych ward where Alan wound up following a mental breakdown triggered by Charlie’s demise.
The acclaimed actress guested as Charlie Harper’s ghost in the memorable Season 9 installment, “Why We Gave Up Women.” Following Alan’s minor heart attack, Charlie tricked Alan into moving out of the Malibu beach house, something he was never able to do while he was alive. The performance won Bates her first Emmy in 2012. (Watch clip.)
The Seinfeld star played Dr. Goodman, an adulterous cardiologist Alan visited in Men’s 200th episode.
Before her Transformers days, Fox was Berta’s spoiled granddaughter, Prudence, to whom Jake took an immediate liking in the Season 1 episode, “Camel Filters and Pheromones.”
ELVIS COSTELLO AND SEAN PENN
In the Season 2 premiere, “Back Off Mary Poppins,” the Grammy Award winner and multiple Academy Award winner portrayed themselves as part of Charlie’s monthly guys’ support group.
In the 10th season finale, the former Disney star guest-starred as Walden’s Instagram-obsessed date. When it turned out the tech billionaire had little in common with the dimwitted beauty, he wound up romantically involved with her grandmother. (Watch clip.)
MICHAEL CLARKE DUNCAN
The late actor made a memorable appearance in Season 6 as an intimidating new neighbor named Jerome. When Jake took an interest in his daughter, it was up to Charlie to cover for his nephew. (Watch clip.)
JENNA ELFMAN AND THOMAS GIBSON
Elfman stopped in as Frankie, Alan’s first love interest after breaking up with Judith, in a Season 1 two-parter. She returned in the rebooted Ashton Kutcher-led Men premiere alongside former co-star Thomas Gibson as Dharma and Greg considered buying Charlie’s home. (Watch clip.)
The Full House alum appeared in Kutcher’s debut episode as a potential beach-house buyer, but backed out after remembering a drunken threesome with Charlie. (Watch clip.)
Charlie set up Alan with the model-turned-actress, who played a neighbor seeking to settle down with the right guy, in Season 4. Once Charlie discovered her promiscuous past, he attempted to lure her away from his brother.
The current momma to Gotham’s Oswald Cobblepot stopped by Men for two episodes during its sixth season, portraying Melissa’s stoner mom who nearly wrecked her daughter’s relationship by inviting a plastered Alan to share her bed.
Before her time in Wisteria Lane, the Desperate Housewives star played Judith’s competitive sister, Liz, in Season 1. While visiting for Jake’s birthday, she planned on seducing Alan to anger her uptight sister.
The former Not Ready for Primetime Player guest-starred as Charlie’s jingle-writing archenemy, Archie Baldwin, in the Season 3 episode, “The Unfortunate Little Schnauser.” (Their beef? Baldwin had a history of beating Charlie out for advertising awards.) (Watch clip.)
The popular Latin singer appeared in Men’s fourth season as a handsome repairman who stole away the attention of Charlie’s girlfriend.
In a Season 1 episode, the current NCIS: Los Angeles star was a former beau of Charlie’s who made the transition from Jill to Bill. (Watch clip.)
In Season 5, Agents of S.H.I.E.L.D. ass-kicker stuck around for four episodes as one of Charlie’s first age-appropriate girlfriends, a respected judge and adjunct law professor named Linda.
The beloved sitcom vet stopped by in Season 3 as an elderly next-door neighbor Alan bedded in hopes of gaining access to her fortune.
Sheen’s former Spin City co-star appeared in Men’s freshman season as Alan’s no-nonsense divorce attorney who lacked impulse control and slept with Charlie. Once Charlie called things off, she made Alan’s divorce proceedings a living hell, granting ex-wife Judith everything she wanted.
After he was Hercules, Sorbo portrayed Kandi’s father midway through Season 3.
The Curb Your Enthusiasm favorite played Charlie’s accountant midway through Season 1, delivering the bad news that the eligible bachelor had to cut back on his expenses.
The popular character actress, most recently of TV Land’s Jennifer Falls, was Jake’s naive teacher, Ms. Pasternak, who had a one-night stand with Charlie in Season 2. When the devout Christian realized Charlie wasn’t looking for anything serious, she went nuts and lost her job at the school.
TV’s go-to guest star showed up as Charlie’s manager, Artie, when the womanizer became a popular children’s songwriter in Season 5.
The Less Than Perfect star played Berta’s pregnant daughter, Naomi, in Season 4. Alan took a liking to her, and the two dated temporarily when Rue reprised the role later that season.
DENISE RICHARDS AND MILA KUNIS
Sheen’s former wife and Kutcher’s current beau have both put in some Men time. Richards was Lisa, the one who got away for Charlie in seasons one and two; Kunis played Vivian, a free-spirited stranger Walden invited into his home and grew enamored with in no time at all, during Men’s penultimate season. (Watch clip.)
After guest-starring as Herb’s sister Myra in Season 4, the Married star returned in a recurring capacity in Seasons 9 and 10 as Walden’s ex-wife, Bridget.