Just when you thought that every kind of list had been done to death, along comes someone with a relatively untapped idea for a new one. The latest brilliant idea comes from SPIN, in the form of the greatest "fictional" songs ever.
Of course no reader is ever going to agree with all the choices and rankings on any list, but this list is more problematic than most in that regard. I see a lot of pet favourites of the writing staff showing up here, in favour of more obvious choices that are more entrenched in pop culture. However, credit goes to them for not falling into anti-modernity trap and choosing mostly songs that are 20+ years old, for picking from a variety of interesting sources (live action comedies, animated TV shows, mockumentaries, etc.), and for nearly sticking to a one song per "artist" rule (the only show with more than one pick on the list is "The Simpsons", unless you group the three Beatles rip-offs into one unit. And three Beatles tributes/thieveries is at least one too many).
Some of their picks seem to run counter to their own rules, for instance the picks from "Hedwig and hte Angry Inch" and "The Producers" run counter to the "no musicals" rule in my book. Now technically you could claim that they only excluded examples where "characters break into song outside of a performance context". In other words, musical numbers where the characters shift from dialogue to song while standing in the street don't count, but put those same characters in a band or on a stage and they're in. That's a seriously problematic dividing line, and even if you accept that logic then as noted by one commenter, "Time Warp" from the Rocky Horror Picture Show would be an inexcusable omission.
Putting aside my own favourites/biases ("The Wedding Singer", HIMYM, "This Is Spinal Tap"), the rankings should favour songs that could be played on the radio, or even are played on the radio, without coming off like novelty songs from a TV show or movie. In other words, songs that transcend their source and have been accepted into the canon of "real" songs. By that measure, the top two are solid picks. You could argue that The Heights' "How Do You Talk To An Angel" should have been much higher, seeing as it went to #1 on the actual Billboard charts. For anyone who wasn't around at the time, its extraordinary success was inexplicable then and it's still inexplicable now. It wasn't riding on the back of the popularity of a TV show (this explains "Do The Bartman" hitting #1) because the show wasn't even a hit and in fact would be cancelled very soon after the song hit #1. It stayed at #1 for one flukey week and then sank from the charts like a stone, and has been more or less forgotten. Plus, the song sucks, so I'm not going to complain that it couldn't crack the top 20 of this list.
If choosing between The Archies and the Wonders for #1, I personally would have chosen the undeniably classic "Sugar Sugar". But you can make a very good argument for "That Thing You Do". The movie is a fondly remembered minor classic, and the song hits exactly the right notes, and more importantly, is completely believable in its role as the perfect top ten hit for the time and place it's supposed to be capturing. For all of the other songs on the list, the song adds a bonus element to the movie/episode that puts it over the top as something even more memorable. But without the perfect song to represent "That Thing You Do", there simply is no movie at all.