Among Will & Grace‘s many legacies—its near perfect cast, its status as one of the last truly great multi-camera sitcoms, and the not insignificant matter of trailblazing LGBT representation—is its knack for snagging some of the biggest guest stars on television. Almost everyone in Hollywood wanted to drop by Will’s Riverside Drive apartment. The show featured Alec Baldwin‘s first real recurring gig on a sitcom years before he’d play Jack Donaghy. Comedy legends like Gene Wilder, John Cleese, and Lily Tomlin appeared. Doyennes of stage (Patti! Bernadette!) and screens big (Debbie! Glenn!) and small (Candice! Joan!) all came to play. Yet, no category of guest star in the Will & Grace universe brought quite as much excitement to the show as that of the pop star. Forget VH1 Divas Live—if a pop star didn’t send Jack into a tizzy or share a few drunken adventures with Karen, can they really be considered a true legend of our time?
Here, we take on the task of not only revisiting but ranking the show’s major musical meetings, which can only be totally subjective, though we did try to weight for objective matters like how long the star appeared and how much was asked of them in their performance. Of course, this begs the very important question of what pop divas we hope to appear over the (at least) two seasons of the show’s revival that kicks off tonight at 9 p.m. on NBC.
7. Barry Manilow as Himself (2003)
In the show’s sixth season, Will, a huge “Fanilow,” spends most of an episode waiting in line for tickets to Manilow’s annual holiday concert. While waiting in line, Will gets hit on by a bear played by Chris Penn. At first, Will rebuffs the advances until he finds out he’s actually Manilow’s tour manager. After agreeing to a date with the bear, Will does get to meet Manilow at the end of the episode. It was a short but sweet moment, but one that also makes us hope for a better representation of bears in the reboot.
6. Elton John as Leader of the Gay Mafia (2002)
While some are surprised that the Will & Grace reboot will tackle current events, the show has, in fact, always made a habit of slyly commenting on the controversies of the day. For example: In 2002, CAA founder and former Walt Disney Co. president Michael Ovitz, who had suffered one of the most humiliating falls in Hollywood history, gave an infamous Vanity Fair interview where he blamed his downfall on the nefarious and secretive workings of a “Gay Mafia” led by David Geffen. Will & Grace responded by casting Elton John as the leader of a Gay Mafia organization whom Jack is convinced has it in for him. Will, of course, doesn’t believe it until he has a run in with John, who reminds him he could have him banned from every gym in America. It’s a smart use of the musician, but clocking in at just over a minute, it’s one of the shorter guest appearances on the list.
5. Janet Jackson as Herself (2004)
After Jennifer Lopez let’s Jack go as a backup dancer (more on that later), she sets him up with a gig as one of Janet Jackson’s six backup dancers. Jackson, however, suddenly realizes there’s just something that sounds right about the number five, and decides to let one dancer go. Jack is forced into a Pennzoil-sponsored dance-off with a veteran dancer played by Will Arnett (who was then relatively unknown because Arrested Development was on the air at the time but no one was watching it). Jackson only has a few lines, but the highlight of her appearance is her dance moves.
4. Madonna as Liz (2003)
Madonna, who claimed not to own a television set at the time, was convinced to do an appearance on Will & Grace after being sent tapes, but declared a) she wouldn’t play herself b) she wanted to do her scenes with Megan Mullally. Thus, we get “Liz,” a character who is apparently meant to be the exact opposite of Madonna in every way: she’s an unsuccessful office manager, has paper thin confidence, has no natural dancing ability, is neither charming nor funny, and does not seem to ever have the upper hand with men at any time. Hell, Madonna plays games of Truth or Dare, while Liz really has a thing for playing True or False. Naturally, Karen, after realizing she’s missed out on so much after visiting a laundromat for the first time in her life, decides to get a roommate and ends up moving in with Liz. It goes swimmingly until they both set their sights on the same Red Bull-swilling, Dockers-wearing man.
3. Jennifer Lopez as Herself—or Jennifer Lopezowitz, if you want to be technical. (2004)
Jennifer Lopez practically did a whole arc on the show that spanned two seasons. She first appeared in the two episodes that made up season six’s season finale. The cast was in Las Vegas for Karen’s wedding to Cleese’ Lyle Finster, when the bride-to-be runs into pop sensation and, incidentally, Rosario’s old friend, Jennifer Lopez in the hotel bathroom. Lopez agrees to perform at Karen’s wedding (although only “Classic J.Lo” is allowed), but when a backup dancer twists his ankle, Jack takes on the job. When season seven rolled around, it was revealed that Lopez was still hanging around and was now Jack’s best friend (her new “J.Mo” in Karen parlance). In the show, Lopez is just another down-to-earth New York City girl who likes to take the subway, is secretly Jewish (the family name was changed from Lopezowitz at Ellis Island), and prefers not to do business with her friends. Thus, Jack is fired, but Jenny makes it up to him by getting him a gig with Jackson. Lopez’s biggest laugh comes when the star, then noted for her stormy love life, finds out Karen’s marriage ended after only 20 minutes and asks, “And that’s short, right?”
2. Britney Spears as Amber-Louise (2006)
Britney Spears may not be the most natural actor of the many divas on this list, but she deserves credit for being game for one of Will & Grace‘s riskiest and most subversive guest spots. To set the scene, Britney Spears appeared on the show in 2006, when she was with Kevin Federline and had recently given birth to her first child. At that time, America was at war in Iraq, and Fox News was in the midst of its first era of power. Spears, maybe trying to shake her unfortunate (albeit, in retrospect, mean spirited) unauthorized appearance in Michael Moore’s documentary Fahrenheit 9/11 defending President Bush, appears as a shameless conservative pundit named Amber-Louise. The setup is that Jack, as you may or may not remember, is enjoying his gig hosting a late night program on OutTV, but OutTV is bought by the conservative Nimbus broadcast (which is itself a division of the Department of Homeland Security, which in itself is owned by Nabisco). Producers gradually push out Jack in favor of Amber-Louise’s right wing rhetoric. As it turns out—do 11-year-old television episodes need spoiler alerts?—she’s actually a “hardcore lesbian” named Peg who’s just in it for the money and fame. “I’m into leather play, butch black girls, skunkin’, pullin’ the blinds, and poodle balling,” says Spears. “Whatever you got, I’ll eat it, snort it, or ride it, baby.” Of all the pop star cameos, maybe the one we most want to see a re-appearance of in the reboot is Amber-Louise/Peg. Hopefully, by now, she has a viral Facebook show where she yells about “snowflakes” but is secretly dating a cast member from Orange Is the New Black on the side. Or maybe she’s hosting the third hour of Today. Who knows.
1. Cher as Cher (2000) and God (2002)
There are two things we know for sure about Cher. 1) She always does everything first (as is true of her Will & Grace cameos). 2) When making an arbitrary and tongue in cheek list of pop star rankings it is best to just go ahead and put Cher as the top, because honestly, it is usually true.
Cher first appeared in the show’s third season as herself. In the episode, the singer and actress runs into Jack (who has spent the better part of the episode manically attending to his Cher doll to the point of making sure it has a booster seat at restaurant). When Jack sees the real Cher, however, he thinks that she is a mediocre drag queen and that his Cher impression is actually better. That is, until he gets slapped by Cher herself. Cher would appear two years later as God (“well, depending on which bath house your worship at”) to persuade Jack not to give up on his entertainment dreams for the fancy new job he just got at Barneys. It’s a tough decision for Jack, but with the help of Cher, her speedo-clad angel backup dancers and a Moonstruck joke, he decides to give performing another chance. Jack’s re-born career as a performer ultimately creates the storylines for many other pop stars on this list to appear on the show—yet another way in which Cher truly paved the way for all those who came after her.
Who’s Next to Carry on the Tradition?
The show has not yet announced any major musical guests, but clearly, the reboot deserves nothing less than a Beyoncé and Lady Gaga joint appearance we not only all crave but desperately need right now, and we’d be surprised if Katy Perry, Ariana Grande and Miley Cyrus hadn’t at least made a note to her managers to ask. Oh the other hand, maybe it’s Rihanna and Nicki who would be the most exciting guests. While it seems like a shocking oversight that Bette Midler and Mariah Carey never appeared in the original, if the show does not feature an episode where Jack becomes so obsessed with Carly Rae Jepsen to the point that he starts seeing her in visions at night, then clearly it has not been keeping up with the gay times and we have no idea why they even bothered rebooting it in the first place.
Jennifer Lopez Has Never Wanted To Blend In: