Whether they’re appearing as themselves or portraying a minor role, it’s always a pleasant surprise to see famous singers on our favorite TV sitcoms. It’s nothing new, considering that musicians have been making appearances in shows for a while now (anyone else recall Aaron Carter’s amazing cameo in Lizzie McGuire??). But even so, it’s refreshing to see these singers get out of their comfort zones and explore the world of acting.
What’s even more rewarding about these appearances, though, is how the characters react when the stars appear as themselves. We don’t know about you guys, but very few things are more satisfying than watching your favorite characters fangirl over a pop star while you’re freaking out IRL.
17. Madonna guest starred on Will & Grace
She appeared in the episode “Dolls and Dolls,” where she played an office worker and Karen’s temporary roommate, Liz. Madonna actually requested that she work alongside Megan Mullally’s character. And during the taping of this episode, she had to film her entrance scene twice because the audience kept cheering so hard. She said, “I had to wait too long to say my first line, so we had to do it over.”
This was Madonna’s episodic television series debut, but according to her manager, the purpose wasn’t to show off her acting skills. She actually did it to promote her 2003 album, American Life.
16. Jennifer Lopez guest starred on Will & Grace
Jennifer appeared as herself on season seven for the episode “I Do. Oh, No, You Di-in’t.” Karen encountered her in the bathroom and convinced her to sing for her upcoming wedding. But before her performance, Jennifer had to recruit Jack to replace a backup dancer who slipped and got injured. At the wedding reception, he got to dance with her while she performed a remixed version of her 1999 single, “Waiting for Tonight.” And because of his successful performance, Jennifer actually asked him to join her on tour.
In one interview, Jennifer explained the meaning behind that one scene where she met Karen for the first time and mistook her for an employee because she was “white.” That joke was actually meant to point out the ridiculous Latina stereotype of always being the “help.”
15. Janet Jackson guest starred on Will & Grace
On the episode “Back Up, Dancer,” Jack auditioned to work with Janet Jackson. The audition was set up by none other than J. Lo, whom he worked for previously. But this time around, he had to fight for the final spot by competing against another dancer.
Janet admitted that while she was excited to make an appearance on the show (she’s a big fan!), it was way more difficult than she expected. She said, “I flubbed my lines and got so frustrated when I made those mistakes. I haven’t done TV since Different Strokes, and it’s not like Saturday Night Live where you can read cue cards. On Will & Grace, they’re always rewriting, so you’re always memorizing.” We can imagine how annoying that was, but we’re so glad that she stuck with it!
14. Cher guest starred on Will & Grace
The singer actually appeared on the show more than once. The first time, she appeared as herself in “Gypsies, Tramps and Weed,” where Jack encountered her at a restaurant and mistook her for a drag queen. But the second time, she appeared to Jack in a dream in what looked like heaven in the season four finale.
For her very first appearance on season three, Cher revealed that she filmed different versions of her scene. She said: “We did two endings. I improvised one. I hope they show it as an outtake ’cause the audience loved that one more than the one they’re gonna show. Instead of the thing I was supposed to do, I did something to Sean [Hayes] – something completely different and he just about passed out. I don’t know what possessed me.”
13. Destiny’s Child guest starred on Smart Guy
The iconic girl group guest starred on the episode “A Date With Destiny.” When T.J.’s big sister, Yvette, auditioned to be Destiny’s Child’s backup dancer, T.J. actually stole the spotlight and got hired by the group instead. He even got an offer to tour with the girls, but seeing as how he was just a kid, his dad wasn’t very supportive of the idea. Aside from performing with T.J., the singers also got to go to Marcus and Mo’s high school dance and perform. It was one of our favorite episodes by far!
12. Jesse McCartney guest starred on The Suite Life of Zack and Cody
Oh, how we miss the good old days when Jesse McCartney still had blond hair and a bowl cut. On season one’s “Rock Star In The House,” Jesse visited the Tipton Hotel as himself. This caused Maddie and London to fangirl like crazy and practically stalk the guy (I mean, wouldn’t we all?!). Meanwhile, Zack kept trying to make money off of his things. So hilarious!
11. Paula Abdul guest starred on That’s So Raven
This was such a fun episode! On “The Road To Audition,” when Raven had a vision that a scout from the fictional Undercover Superstar would be visiting her school, she and her friends went out of their way to impress the undercover janitor (portrayed by Paula). It’s a musical episode that featured numbers by Raven-Symoné, Orlando Brown, and Anneliese van der Pol. Oh, and here’s a fun fact: The episode was directed by Debbie Allen!
10. Cyndi Lauper guest starred on That’s So Raven
The ’80s pop star played Chelsea’s art teacher, Ms. Petuto in “Art Breaker.” This was the episode where Raven accidentally broke Chelsea’s life-sized statue of her (which included a huge beak). Cyndi Lauper could’ve totally reprised her role or at least made more appearances because she played Ms. Petuto so well. (BTW, we almost died laughing when she observed Chelsea’s statue without realizing it was really Raven!).
9. Prince guest starred on New Girl
Prince actually enquired about making a guest appearance because he loved New Girl so much. The late singer got to contribute to script and he even debuted a song, which featured vocals from Zooey Deschanel. Since this was also set to air right after the Super Bowl, it became one of the most expensive episodes to shoot. Other guest stars included Clayton Kershaw, Alessandra Ambrosio, Ana Beatriz Barros and Lais Ribeiro.
During the actual episode, Prince helped Jess and Nick reach a huge milestone in their relationship. He was the one who inspired them to reveal how they really felt by saying “I love you” for the first time (and we were all so there for it).
8. Aaron Carter guest starred on Lizzie McGuire
Guys, this episode was pretty much the definition of iconic. Like, just the thought of that scene where Aaron kissed Lizzie under the mistletoe and told her ‘Merry Christmas’ still gives us goosebumps. In “Aaron Carter’s Coming to Town,” Lizzie and her besties learned that Aaron was filming his music video for “I Want Candy” nearby. And so what did they do? They snuck on to his set like any hardcore fan would, of course. If we had to rank the best episodes of this show, this would easily make the top three.
7. Eve guest starred on Glee
She played Grace Hitchens, the strict director of the Jane Addams Girls Choir in “Hairography.” After the late Whitney Houston declined to take part in the show, Eve agreed to do two episodes. She stated: “I got asked and I’d heard the buzz about the show. When the first pilot episode came out, I figured it was something different and something we haven’t seen on TV before. I didn’t want to turn it down!” And we’re so glad that she didn’t, it was interesting to see her chemistry with Mr. Schue!
6. TLC guest starred on Living Single
This one’s a throwback! TLC appeared as themselves in a few dream sequences on “The Following Is a Sponsored Program.” After Overton fell asleep while watching a TLC music video, the “No Scrubs” singers started to show up in his dreams. He wound up feeling really guilty about it because of his girlfriend, Synclaire, but then, after the trio convinced him that dreaming about them was not cheating, they moved on to Kyle’s dreams. (I mean, duh! You can’t control your dreams.) Very intriguing…
5. Monica guest starred on Living Single
This R&B; singer played the sister of Khadijah’s then-boyfriend, Teddy, on “Kiss Of The Spider-Man.” He’d asked her to help his sister through a recent breakup, but that proved to be a challenge when she overstayed her welcome and nagged them constantly. Though her character was definitely annoying, we kind of wish that she had more screen time. Her acting skills were pretty good and she turned out to have some of the funniest scenes of the episode!
4. Brian McKnight guest starred on Martin
As Martin prepared to propose to his girlfriend Gina on the episode, “Love Is In Your Face,” Brian McKnight stepped out and started to sing “Never Felt This Way.” This came after the two had gone through a rough patch and Gina was considering leaving him for good. But it’s safe to say that Martin went above and beyond to win her back. It was one of the most romantic moments we’ve ever seen on TV (and yes, it still gives us all the feels).
3. Outkast guest starred on Martin
The duo got to perform at the Player’s Ball on season three’s “All The Players Came.” It turned out that one of Martin’s favorite theaters was shutting down, and so he put together a fundraiser to help save it. As the credits began to roll, Outkast performed their song “Player’s Ball” (which most likely inspired the event’s theme). And aside from the famous duo, Martin got other famous names to participate, including Pam Grier, Antonio Fargas, and Coolio.
2. Boyz II Men guest starred on Fresh Prince of Bel-Air
The group appeared on an ep called “Twas the Night Before Christening,” where Little Nicky had his Christening Ceremony on Christmas Eve. Will felt so intimidated by the Banks family’s expensive gifts for Nicky that he promised to get a live, personal performance by Boyz II Men to out-gift them. He made several attempts to get the group to sing for Nicky (who happened to be a huge fan), but it seemed like the group had no intention of helping him out. Still, at the very last minute, they actually showed up and performed “Silent Night.” Those vocals were *literally* everything!
1. Britney Spears guest starred on How I Met Your Mother & Glee
If you’re a fan of How I Met Your Mother, then you’ll remember Britney as Abby, the naive receptionist who had a major crush on Ted. On “Ten Sessions,” she failed to win over Ted and ended up having a one-night stand with Barney. But in her final appearance (“Everything Must Go”), she pretty much became Barney’s personal saboteur. By the end, they’d reconciled and they were this close to getting engaged, but Barney was able to lie his way out of it (of course).
As for Glee, the show paid homage to the iconic singer in “Britney/Brittany,” where she appeared as herself. The show’s creator, Ryan Murphy, mentioned that it was Britney’s idea for her songs to be used, saying: “I think she loves what the show’s about, paying tribute to pop culture in a very loving, respectful, kind way. She responded to that.”