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Before Brit: Memorable ''Will & Grace'' guest stars

Britney Spears’ visit to ”Will & Grace” inspires a countdown of the 10 most memorable guest stars on the series

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Will & Grace: Chris Haston

Before Brit: Memorable ”Will & Grace” guest stars

Britney made it in just under the wire: Her appearance on the March 30 episode of Will & Grace as Amber-Louise, a cohost foisted upon a reluctant Jack (Sean Hayes) by his channel’s conservative new owners, will be one of the last in a long line of illustrious guest spots on the soon-to-end sitcom. The seemingly endless parade of A-listers and icons who’ve played fifth wheel to the Will/Grace/Jack/Karen quartet has been a standout feature of the show — albeit one that’s made critics complain it’s turned into a gimmicky, sitcom Love Boat. Still, the series remains a top draw for visitors, including movie royalty who seldom do TV (Michael Douglas, Matt Damon) and tabloid fixtures supposedly trying to keep low profiles (J. Lo, Janet Jackson, and Spears). As W&G approches its May 18 finale, look again at the reruns (we did), and you’ll see that a lot of these self-parodying one-shots have been surprisingly funny. A countdown of the most memorable cameos follows.

Image credit: Will & Grace: Chris Haston

Madonna

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Memorable ”Will & Grace” guest stars: Madonna

The mercenary nature of the Will & Grace guest spot has never been more apparent than in Madonna’s appearance, timed to coincide with the promotional push for her 2003 American Life album. On the sitcom, Madonna played Liz (the name is an apparent homage to Madonna’s longtime publicist, Liz Rosenberg), an eccentric woman who briefly takes on Karen (Megan Mullally) as a roommate. It’s not a performance that’ll erase memories of Swept Away or other bad Madonna acting — the singer delivers her lines as if in a trance, with her eyes half-lidded — but it’s weirdly compelling just the same. Plus, Madge proves a good sport: She lets Mullally fondle her breasts.

Image credit: Will & Grace: Chris Haston

Janet Jackson

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Memorable ”Will & Grace” guest stars: Janet Jackson

This 2004 guest spot marked Jackson’s first prime-time TV appearance since her Super Bowl fiasco — and her first sitcom work since she made her name as a child star on Good Times and Diff’rent Strokes two decades earlier. Miss Jackson is all business, playing it straight in a plot that sees Jack, fresh from his stint hoofing for Jennifer Lopez, competing for the last open slot as one of Jackson’s backup dancers. His rival is an ex of Karen’s (played by Arrested Development‘s Will Arnett). In the end, Jackson cuts them both, but she makes a fabulous entrance and departs with her dignity intact — not a single wardrobe malfunction joke is heard.

Image credit: Will & Grace: Chris Haston

Jennifer Lopez

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Memorable ”Will & Grace” guest stars: Jennifer Lopez

J. Lo wasn’t above poking fun at her own much-married status in the season 6 finale, when Karen asks her to perform at her own abortive wedding. Lopez returned for the ending of that cliffhanger, the season 7 premiere, in which Karen tries to get J. Lo backup dancer Jack to help her pitch the pop star a song she’s written called ”FYI: I Hurt Too.” No wonder Lopez fires Jack, though she makes it up to him by getting him the Janet Jackson gig. See, she’s not a diva.

Image credit: Will & Grace: Chris Haston

Suzanne Pleshette

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Memorable ”Will & Grace” guest stars: Suzanne Pleshette

The casting directors on W&G have had a spectacular eye when it comes to picking actors to play the stars’ parents, including Debbie Reynolds and Alan Arkin as Grace’s folks and Blythe Danner and Sydney Pollack as Will’s. So it was with Pleshette, who appeared as Karen’s estranged con-artist mom (in a 2002 two-parter and again in 2004). Pleshette’s low rasp makes a fine counterpart to Mullally’s squeak, and her character’s manipulative streak and blithe self-absorption — she sees her wealthy daughter as her ticket out of a barmaid job in Yonkers — explain a lot about the origins of Karen’s chirpy callousness. Plus, it takes a big personality to make the broad, irrepressible Karen look like a trembling little girl.

Image credit: Will & Grace: Chris Haston

Cher

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Memorable ”Will & Grace” guest stars: Cher

Cher appeared twice on the show — once in 2000, when Jack mistook her for a drag-queen Cher impersonator, and again in a more flattering appearance in 2002’s season 4 finale. In the latter episode, Jack contemplates quitting showbiz until Cher appears to him in a dream sequence set in heaven — a dream that climaxes with a musical number performed by the star and some hunky, nearly nude angels. ”You’re hawking your album during my dream!” complains Jack. Replies Cher, ”Somebody’s gotta pay for the fog and the dancing fairies.”

Image credit: Will & Grace: Chris Haston

Edie Falco & Chloe Sevigny

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Memorable ”Will & Grace” guest stars: Edie Falco and Chloe Sevigny

As apartment ”flippers,” Manhattan Westsiders Will (Eric McCormack) and Grace (Debra Messing) meet their match in Deirdre (Falco) and Monet (Sevigny), a rival real estate/interior-design team from the tony Upper East Side. Oh, they’re also a lesbian couple. This 2004 episode sees the two competing pairs fight an escalating war of sexual divide-and-conquer, one that nearly finds both Will and Grace, um, switching teams. Neither Falco nor Sevigny has ever been more alluring, but in the end, nobody flips to the other side.

Image credit: Will & Grace: Chris Haston

Michael Douglas

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Memorable ”Will & Grace” guest stars: Michael Douglas

Douglas throws himself with gusto into the role of Gavin, a newly out cop who invents an elaborate ruse to get closer to Will. But Jack, acquainted with Gavin from a support group, knows his secrets, including his phobic disgust for people with food stuck in their teeth. His slow-dance with Will makes for a wonderfully touching sight gag. For being so game in this 2002 episode, Douglas earned an Emmy nomination.

Image credit: Will & Grace: Chris Haston

James Earl Jones

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Memorable ”Will & Grace” guest stars: James Earl Jones

In what may have been his easiest acting gig since ”This is CNN,” the booming-voiced actor plays himself in a 2003 episode. In search of inspiration, he takes Jack’s acting course and gets in touch with his feminine side. (Priceless moment: Jones performs a stage exercise as Carrie from Sex in the City.) Fortunately, Jones eventually comes to his senses and quits the class; after all, he remembers, ”I’ve got Darth Vader money.”

Image credit: Will & Grace: Chris Haston

Matt Damon

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Memorable ”Will & Grace” guest stars: Matt Damon

If you’ve ever wanted to hear Matt Damon sing, this 2002 episode is the one for you. He plays Owen, Jack’s rival for a solo spot in the Gay Men’s Chorus. He’s also a ringer; despite his protestations that he’s ”as gay as the locker room at the Ice Capades,” Owen is just a straight guy who likes choral music. Jack outs him in front of the rest of the singers after catching him in a compromising position with Grace (whose seduction of Owen goes comically awry), but the move backfires: The choir accepts Owen anyway out of tolerance. (And because he’s hot.)

Image credit: Will & Grace: Chris Haston

Kevin Bacon

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Memorable ”Will & Grace” guest stars: Kevin Bacon

The famously ubiquitous actor appeared as himself in 2002, in an episode where he hires Jack as a personal assistant and asks him to find the identity of the star’s stalker — who is, of course, Jack himself. To Jack’s horror, it’s Will who gets to share a fantasy moment with Bacon, as the pair bust some moves together in a Footloose-inspired dance. ”The bastards wanted to hire a dance double,” Bacon told EW at the time. ”But Eric stood up for me. He said, ‘I think the old boy can still do it.”’ As it turns out, he can.