Tonight's Parks and Recreation features a cameo from First Lady Michelle Obama, which is all well and good. It also features appearances by Yo La Tengo, Jeff Tweedy, The Decembrists and others as part of a music festival thrown by the show's characters. Here, Parks is wading into much trickier territory, which has dogged good and bad shows alike—when you invite a "cool" band onto your show, are you hopelessly dating your show forever and ever? I like Yo La Tengo and Jeff Tweedy, but it could easily be argued that both are out of their primes at this point. There are too many examples of this troubling phenomenon to comprehensively cover, but we picked out some juicily embarrassing examples.

Rooney, The O.C.

It made sense that The O.C. featured a good hundred thousand bands performing live on the show in its four seasons. The show was so geared around its soundtrack albums, and the first pop hits to provide backing tracks for the show were pretty much ripped right from creator Josh Schwartz's iPod. But the guest appearance by the basically unknown Rooney in the first season was the first and most memorable time Schwartz pointed his cameras at a band he enjoyed. Memorable mostly because no one had ever heard of Rooney, but everyone on the show is so excited to see Rooney. Rooney! The episode has a little fun with the fact that lunkhead Luke gets very excited despite having obviously never heard of Rooney before, but I sympathize with the guy. To this day, I could not tell you one thing about Rooney.

The Shins, Gilmore Girls

It's worth noting that this guest appearance came a good six months or so before Garden State came out and The Shins saved Natalie Portman, Zach Braff, and everyone else in America's lives. But this is another form of musical guest appearance that I just cannot abide. We're just suddenly treated to a four-minute concert from some band we might or might not care about. It feels like a more artistic form of product placement, and no matter how much I enjoy the band, it's almost always disruptive to the episode. Gilmore Girls also did this with The Bangles in the first season, structuring a whole episode around a Bangles concert, but that was just too dorky to hate.

Aimee Mann, The West Wing

Any time a musician who wasn't Yo-Yo Ma appeared on The West Wing, it was trouble. There's more than one episode that staged Rock the Vote or innauguration concerts to shoehorn some beyond-lame musical act like Jon Bon Jovi or the Foo Fighters into an episode, never for any good reason other than the sake of it. Aimee Mann's fame never reached those heights, but the awkward cut to her performance in this episode has provoked loud laughs from me on multiple occasions. The cameo from the House of Blues itself is honestly just as cringe-inducing.

Everyone, The Simpsons

The Simpsons has been on the air for at least ten years too many, and has featured guest appearances from musicians more times than many shows have aired entire episodes. Just as with all guest appearances on The Simpsons (and everything else on The Simpsons), attempts to work bands into storylines have gotten lazier and lazier. Sometimes they just show up with no explanation and perform a song; sometimes they don't even do that, just walking on screen to dispense a funny line. The Simpsons' extreme length has made a guest appearance on the show something of a rite of passage, a sign that you've made it to the big show, like a mini-version of a star on the Walk of Fame. Everyone has to get it out of the way.

10,000 Maniacs, Sabrina the Teenage Witch

This show was doomed from the get-go because it was about a teenager with magic powers. So Sabrina can (and often does!) summon any band she likes to her house to play her an impromptu concert. But I'll never forget the time she summoned 10,000 Maniacs (somehow including Natalie Merchant!) to cap off her Halloween party. And then cool kid Asher, who wears a leather jacket, turns around and goes, "Whoa! It's the 10,000 Maniacs!" Sigh. Just watch the clip and feel yourself age by a thousand years.