Once Charlie called things off, she made Alan’s divorce proceedings a living hell, granting ex-wife Judith everything she wanted. Sheen’s former Spin City costar appeared in Men’s freshman season as Alan’s no-nonsense divorce attorney who lacked impulse control and slept with Charlie. 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. 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. In a Season 1 episode, the NCIS: Los Angeles star was a former beau of Charlie’s who made the transition from Jill to Bill. The popular Latin singer appeared in Men’s fourth season as a handsome repairman who stole away the attention of Charlie’s girlfriend. 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.) While visiting for Jake’s birthday, she planned on seducing Alan to anger her uptight sister.
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TV screenshot TERI HATCHERīefore her time in Wisteria Lane, the Desperate Housewives star played Judith’s competitive sister, Liz, in Season 1. 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. Once Charlie discovered her promiscuous past, he attempted to lure her away from his brother. TV BROOKE SHIELDSĬharlie set up Alan with the model-turned-actress, who played a neighbor seeking to settle down with the right guy, in Season 4.
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The Full House alum appeared in Kutcher’s debut episode as a potential beach-house buyer, but backed out after he recalled a drunken threesome with Charlie. 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.
TV screenshot JENNA ELFMAN & THOMAS GIBSONĮlfman stopped in as Frankie, Alan’s first love interest after breaking up with Judith, in a Season 1 two-parter. When Jake took an interest in his daughter, it was up to Charlie to cover for his nephew. ( Watch clip.) The late actor made a memorable appearance in Season 6 as an intimidating new neighbor named Jerome. When it turned out the tech billionaire had little in common with the dimwitted beauty, he wound up romantically involved with her grandmother.
In the 10th season finale, the former Disney star guest-starred as Walden’s Instagram-obsessed date. 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.
TV screenshot MEGAN FOXīefore 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.” Goodman, an adulterous cardiologist Alan visited in Men’s 200th episode. The performance won Bates her first Emmy in 2012. 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 Oscar nominee made a quick cameo in the Season 9 episode, “Frodo’s Headshots.” He was a fellow patient in the psych ward where Alan wound up following a mental breakdown triggered by Charlie’s demise. As it turned out, she had both brothers fooled. TV screenshot PAGET BREWSTERīefore 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. 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.
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