The Song: "Kiss from a Rose" is both corny as hell, as well one of the most romantic songs ever written. It's so undeniably sexy that it's single handedly responsible for convincing Heidi Klum to marry Seal. (I guess it's possible that they had some sort of emotional connection too, but I'm pretty sure it was just the song.)
The Movie: The only reason Batman Forever didn't go down in history as the worst Batman film ever made is that Joel Schumacher made a sequel. The campy crapfest was the beginning of the series' impressive fall from grace, as well as the only reason you've ever heard Seal's biggest hit. Though Kiss From a Rose was not written for the superhero film, it was popularized on the soundtrack. The partnership between the movie and the song also lead to an incredibly strange music video that features Seal singing shirtless in front of the Bat Signal, interspersed with clips of a red headed Jim Carrey. (It's actually pretty awesome.)
The Song: Whether you love it or hate it, odds are you've heard Smash Mouth's magnum opus at least 6 million times. The song's been undeniably overplayed, but there's a good reason for that: It's stupid, annoying, and actually pretty good.
The Movie: If you've ever watched the music video for "All Star," you probably wondered why it has Ben Stiller is in it. If you've never watched the "All Star" video, you've likely led a much richer life than I have. In fact, the Ben Stiller cameos are actually clips from the superhero parody Mystery Men. The largely forgettable movie features Hank Azaria in some questionable brown face, Kel Mitchell in a large supporting role, and a shockingly unfunny cameo from Dane Cook. In other words, the movie that gave us "All Star" somehow manages to be stupider than the song itself.
The Song: If you've never listened to Aaliyah, you should do so immediately. In her tragically short life, she gave the world a bunch of really good and groundbreaking songs. Arguably her greatest achievement was "Are You That Somebody," a song so great that the notoriously picky Pitchfork ranked it the 8th greatest song of the 90s. (FYI, that's 5 spots ahead of "Smells Like Teen Spirit.)
The Movie: If you can believe it, this amazing song was written for the Eddie Murphy remake of Dr. Dolittle. If you don't remember this movie, let's just say this: The funniest lines are spoken by a young Raven Symone...Yeah, it sucks butt. Thankfully, the only part of the song the movie ruined is the music video, which, despite trying to be serious and intense, also features scenes of Aaliyah dancing in front of projections of Eddie Murphy's face which...Yeah...
The Song: You know that band Train? Well imagine if they wrote a song that wasn't terrible and you'd have "Iris" by the Goo Goo Dolls. The song was a huge hit in every sense of the word, and for good reason. Anyone with a heart is sure to feel something when they hear the line "I don't want the world to see me, 'cause I don't think that they'd understand."
The Movie: "Iris" was released on the City of Angels soundtrack, which if you've never heard of that before, here's a quick rundown: An angel falls in love with a human, played by Meg Ryan, and decides to stop being an angel to be with her. That angel's name? Nicholas Fucking Cage. Granted, I've never seen the movie so I can't say for sure, but I gotta imagine based on that plot it wouldn't make me well up quite as easily as "Iris" does.
The Song: If you looked up inspirational in the dictionary, it would somehow just start playing "I Believe I Can Fly" by R. Kelly. One listen to this uber-sincere ballad and you'll believe you can do just about anything, including spreading your wings and flying away...Seriously, it's how I broke my arm in the 5th grade.
The Movie: The song starts to feel a little harder to take seriously once you realize that the flying he's talking about involves Bugs Bunny dunking on one of the Monstars. It's very funny to think about how one of the most earnestly uplifting songs in history was written for Space Jam, which has one of the silliest plots in history. That said, this entry might not fit on this list because Space Jam is fucking awesome.