His cameo as former child star Randall Finn now all grown up wasn't much more than stunt casting, way to capitalize on his hot streak at the time.
Gregg's 2003 cameo had him playing Cam, a boy toy of Jack's who was too good (and a little too boring) for the superstar.
Long before he was McDreamy, Dempsey was Will's closeted sports reporter boyfriend Matt. They broke up because Matt wanted to stay on the D.L. for his job which is fine: the role was a snooze.
Remember when she was everywhere? In 2004, Osborne landed a spot as Nonny, a bartender. Don't remember this appearance? Yeah, you're not alone.
A short and silly bit has the soulful duo mistakenly arrive at the sham wedding between Grace and James, Will's boyfriend. Brief though their bit was, they had perfect comedic timing and self-deprecation so if that music thing doesn't work, perhaps they could go on the road doing comedy.
Overshadowed by Britney Spears and George Takei in a celebrity bonanza of an episode, Wanda Sykes played Karen's makeup artist Cricket. That was in 2006; she came out two years later.
Fresh from wrapping Sex and the City in 2004, Kristin Davis played Nadine, best friend to Will's boyfriend Vince. Nadie was painted as sweet with a sinister side, but Davis really couldn't do much to make the spot distinctive from her more famous character, Charlotte York.
As Jason "J.T." Towne, Culkin was Karen's inexplicably young divorce lawyer who's much more savvy than he seems. Funny enough, but fleeting.
His appearance in 2005 as Aaron, a guy Jack and Karen meet in the park, was forgettable.
Fun fact: the silver fox, who played Will's brother Sam, was later replaced by Steven Weber.
Piven played Nicholas, Grace's douchey ex who was pressuring her into a three-way with his current flame. Piven, perhaps not surprisingly, knocked that character out of the park, even if he did shove his tongue "all the way down" to Debra Messing's heart in rehearsals -- as she told Andy Cohen on Watch What Happens Live.
The sandpaper-voiced comedic actor played Lionel Banks, Karen's almost paramour. Not the best use of the legend, unfortunately.
Riding her bombshell persona to the bank, Sheridan played Dr. Danielle Morty, a colleague of Leo's who stuns Grace for not being, well, male and smoking hot. Sheridan, as it happens, auditioned for the role of Grace, the results of which are now clear.
Securing the master showman couldn't have been easy, but the Rocket Man had an absolutely perfect role as the head of the Gay Mafia. Sadly, it was too short to be worth more than a passing fancy.
Matt played Owen, a straight singer posing as straight who's competing with Jack for a spot in the Manhattan Gay Men's Chorus in Stiff as he was, watching him trade shade with Jack was undeniably funny.
Sissy Palmer-Ginsburg, as Demi Moore was known on a 2003 episode, popped up as Jack's old babysitter who had a serious problem with boundaries (and reality). Right before her comeback role in Charlie's Angels, Moore played the part with aloof roboticism -- and not in a good way.
The master chameleon transformed into Ann, a fiery cooking instructor. She was wonderfully loony as ever and yet not on screen nearly enough.
Mira was Leo's glam ex-girlfriend Diane in 2003, stirring up feelings of jealousy with Grace when Leo invited her to dinner...and everyone learned she slept with Will in college. She was fragile and petty, and very funny.
She wasn't as scary and severe as Carmela Soprano, but Deirdre, the apartment-flipper who went up against Will and Grace with her partner Monet, was still pretty intimidating.
In 2001, before she'd become a friend to millions of moms watching her dance on her daytime talk show, Ellen showed up in as Sister Louise, a nun who hustles Will and Grace out of money for an old car that used to belong to Grace's uncle. T'was fun, but nowhere near enough of a showcase for Ellen's outsized talent.
The indie darling -- and LGBT ally -- played Monet, one half of a couple battling Will and Grace in an apartment flipping enterprise alongside partner Deirdre (Edie Falco). Monet was subdued and sardonic -- just like the hipster queen herself.
Way before she was a bad girl on Orange is the New Black, Natasha Lyonne was Grace's young trainee Gillian, who became obsessed with Karen. Lyonne gave Gillian her signature dry bite, standing out among the show's stars.
Just 11 months before her infamous meltdown, Princess of Pop Britney appeared on a 2006 episode of Will & Grace as Amber Louise, a conservative Christian (yet closeted lesbian) talk show host meant to replace Jack on OutTV. Her appearance was a cute way for her to play with her image -- right before she set it on fire.
One of the revival season's first high-profile guests, Platt is the rare millennial actor to have sashayed across the set -- and the role toyed around with his Gen Y status too. He played Blake, the much-younger, annoyingly ADD-addled date of Will. He doesn't have decades of experience like many other Will & Grace guests, but the Broadway star earned a spot as one of the series most memorable.
Playing against type, Glenn Close got wild with Will & Grace as Fannie Lieber, an acclaimed photographer with a unsettlingly eccentric personality. Among her quirks: dry humping people without warning.
Notable for being one of few people of color to appear on the series, Taye was Will's boyfriend James Hanson beginning in the (then) final season. Grace married him so he could get his green-card and he and Will could be together -- and then it quickly fizzled. As for the performance, it was just as so-so as one might expect of two straight dudes pretending to be in a gay relationship.
Oscar winner Alan Arkin played Martin Adler, Grace's Dad. The 2005 episode had him gamely absorbing Grace's whining and Karen's mischievous nonsense with patience and, well, grace.
Sharon Stone played Dr. Georgia Keller, a therapist to both Will and Grace in a 2005 episode that had her playing with her Basic Instinct vixen persona. Unfortunately, that joke had, by then, become a little stale.
Lynch was pitch-perfect as Roberta, a counselor at a camp intended to convert gay kids to straight in an episode from Will & Grace's most recent season. Lynch played the part with the stoic silliness for which she's adored.
The Material Girl and gay icon appeared in 2003 playing Liz, a kooky woman who becomes roommates with Karen. Madonna reportedly loved the show (and the audience loved her, cheering so hard when she entered that she had to wait to do her lines) but critics weren't feeling it. Her over-the-top turn was widely panned.
In a 2002 episode,Rosie O'Donnell played Bonnie, mother of Elliot, the kid Jack didn't know he had as a result of a sperm donation when he was 17. You know Rosie: she was abrasive and caustic cool as always, deftly handling the storyline that had her come out to Jack. A month later, she came out publicly herself.
In the 2002 episode "Fagel Attraction" (a title that's a play on Douglas' landmark film Fatal Attraction), Douglas plays Detective Gavin Hatch, a closeted cop who tries to seduce Will. A highlight: seeing Douglas shimmy to Missy Elliott's "Get Ur Freak On" which was intentionally cringeworthy.
A full 13 years before he officially came out in 2017, Barry Manilow appeared in a episode as himself. The set up was that Will, Barry's biggest fan (a "Fanilow"), turns down a guy who turns out to be Barry's road manager, which of course causes Will beg for the date again. As for Barry, he was exactly what the bit called for: schmaltzy and adorable.
As Artemus, Will Arnett competed against Jack for a spot on Janet Jackson's backup dancer squad in. His part was small, but Arnett threw himself into the bit, serving jazz hands and admirable sass.
Just one year after he came out, George Takei appeared as himself in Season 8. Though he got slightly upstaged by Britney Spears (who was in the same episode), Takei poking fun at his Star Trek roots was just the thing to help cement him as a fabulous and funny gay icon.
Appearing as himself, Kevin Bacon hires Jack as a personal assistant, unaware Jack is also his stalker. As some sort of karmic payback, Will, not Jack, ends up getting to dance with Kevin Bacon in a Footloose-inspired routine. Charming.
A huge fan of the show, Ms. Jackson appeared on Will & Grace in September 2004 -- just months after the Super Bowl fiasco tarnished her career. Jackson played herself, auditioning dancers for a tour. Naturally, Jack found his way into her orbit, battling with a guy named Artemus (played by Will Arnett) for a spot. Just like in real-life, Jackson was soft-spoken but a little bit of a diva -- and though her performance was fun, critics panned it.
In Neil Patrick Harris came on as Bill, a "formerly gay" dude who leads the gay rehab group Welcome Home. As usual, Harris was a gay (in the light and fun sense) delight. The role took on new resonance when he came out as gay himself six years later, in 2006.
Peters appeared on Will and Grace as Karen's sister, Gin. Recipient of "meager" monthly payments to the tune of 300K, Gin is, of course, tragic compared to her fabulous sister, and played with divine grace by the theater hero.
He didn't get an Outstanding Guest Emmy nom like John Cleese, his occasional scene partner, but Curry dazzled nonetheless as Marion Finster, brother to Cleese's Lyle.
Will & Grace featured many an entertainment legend during its run, but none more beloved in the Broadway world than LuPone, who appeared as herself. Like many other guests, LuPone had a part that toyed with her esteemed status, with Jack telling her "Shut up, Patti LuPone!" because he was trying to talk to Will. Unlike other guests though, LuPone stole the spotlight with her brief time on screen, mostly by being steely and cool versus competing with the stars of the show. And she sang! Of course she sang.
Playing herself, the dance and theater maven meet Karen and Jack in a coffee shop , with the actress lampooning her memorable monotone from Frasier. Can she do any wrong? Maybe, but no one would know from this sly cameo.
As Grace's neighbor (and then love interest), Harrelson portrayed unsophisticated goof Nathan. A natural, and fun, fit.
Yes, Molly Shannon's role as Grace's kooky and chemically imbalanced neighbor Val is very close to many other characters Shannon has played but...whatever. She's been reliably offbeat in the five (and counting) episodes she appeared in, and was so good, she came back for the Season 8 revival.
In her three great performances, Lopez skewered almost all the things she's known for, including diva behavior, being a tireless triple threat and even taking the NYC subway.
Yet another renowned performer who appeared on Will & Grace and then later came out, Tomlin played Margot, a partner at Will's firm in two episodes. Tomlin's caustic wit was still very much in fine shape. She came out publicly a full ten years later in 2015, after her mother died, at age 76.
The stalwart screen queen played herself -- a longtime frenemy of Karen Walker who delighted in pulling elaborate, cruel pranks. As to be expected, she killed it. Because she's Candice Bergen.
Posey was unforgettable as Dorleen, Jack's sourpuss boss at Barney's who hated everything -- except the somber Christmas display she thought Jack created (it was really Grace) for a window.
In 2004 Davis came on Will & Grace as Grace's long-mentioned estranged, grifter of a sister who arrived in town to launch a jewelry line. She got her act together by the end of the episode -- a disruption of the natural order that rattled Grace and was later revealed to be the work of Will. Davis, for her part, nailed the role, giving Janet the precise mix of vulnerability, gravitas and crazy the part required.
The icon and personal deity of Jack McFarland appeared on Will & Grace in 2000 when Jack was obsessed with a Cher doll and mistook her for a drag queen, and then again in the 2002 Season 4 finale, when Cher came to Jack in a dream, rightfully playing God. In both, Cher was restrained and mildly entertained by Jack, just as aloof as a diva of her stature should be.
Oscar-winning Pollack had a recurring role as Will's "cool Dad" George. Vulnerable (after it was revealed he'd been cheating on Will's mom) and self-effacing and yes, deadpan funny, Pollack left an indelible mark.
Fabulous of course, Collins played the (did we mention fabulous?) Helena Barnes, Grace's design rival and a barb-trading nemesis of Karen Walker. She was positively regal, and it was everything.
Inspired as always, Cleese guest-starred alongside Tim Curry, as Lyle Finster -- one half of a duo of gonzo brothers. He earned an Outstanding Guest Actor in a Comedy Series Emmy nod for his six-episode arc.
As Jack's acting coach, the veteran actor with the heavy voice shined in the truly absurd role of... James Earl Jones, an actor in need of advice from Jack. Jack taught Jones to "get in touch with his feminine side" by doing a bit as Carrie from Sex in the City, and then he quit the class, proclaiming, "I've got Darth Vader money." Priceless.
The late Emmy and Tony Award-winning tap dance legend had an eight-episode arc in the series, playing Ben Doucette, Will's boss. Ben went on to date Grace and, in a memorable episode, flaunt his world-famous tap dancing skills in a competition with Jack.
Baldwin's turn as Malcolm Windmark marked a milestone for the show: this was its live episode, performed once for the East Coast and again for the West. While other stars occasionally cracked, fumbled and flubbed a line or two, Baldwin was so good as Will's former boss (and a secret agent) he scored an Emmy nom.
Gwyneth Paltrow's mother made Marilyn Truman, Will's Truman's unbearably WASPy mother, one of the series most beloved characters from the moment she arrived. Danner gave Marilyn a sort of vacant, ivory tower snootiness, and was nominated for an Outstanding Guest Actress Emmy for the 57th Emmy ceremony in 2005.
As Vincent "Vince" D'Angelo, the New York City cop who was Will's longtime squeeze, Bobby Cannavale appeared in 16 episodes from 2004-2006. He won an Outstanding Guest Actor Emmy for the role in 2005.
As Leo, Grace's boyfriend and then husband (and later, ex-husband), the musician-actor-everything is back again for Season 9. Which is great: Connick brings gravitas, charm and stability to what can sometimes be a circus.
Wilder, who died in 2016, made his last appearances on Will & Grace in 2002 and 2003. The comedy pioneer played Will's weirdo boss Mr. Stein, doing hilariously wacko jokes and stunts in two unforgettable episodes.
Driver stormed in as Lorraine Finster, the mistress of Karen's husband Stanley. She's one of the series' most outrageous recurring characters: a sex worker, a stripper, an intersex woman whose male parts were removed, a thief born in an alley and, for a brief time, Karen's stepdaughter when Karen married her dad. A constant threat to Karen (and the only woman who could get under her skin with razor-sharp barbs) Lorraine was a hoot thanks to Driver's deadpan delivery and self-depreciative approach.
Playing one of Will & Grace's most beloved recurring characters won Jordan an Outstanding Guest Actor Emmy in 2006 -- and with good reason. Only Jordan could play the totally absurd Beverly Leslie, Karen's short, sworn nemesis with a sugary voice and stereotypically sweet mannerisms. He's a ridiculous treat in every episode he's appeared in. And not for nothing, he's the guy who let it slip the series was returning.
Reynolds dazzled in 12 episodes as Grace's exuberant and passive-aggressive mom Bobbi Adler, high-kicking with panache during her tenure. Reynolds' 2016 death left an irreplaceable hole in Will & Grace, and the team paid tribute to her when the show returned for Season 9.