Disclaimer: The songs picked have to have been good enough to be obsessed with at some point, but not so much that I'm sick of it now. Also, I didn't put jazz standards in since so many people cover those songs. In fact, the list is primarily rock and pop songs with just a dash of country and R&B. And I don't really listen to enough rap or techno or heavy metal to list any of those songs as favorites--sorry fans of those genres. Mostly, this is just to say that this list is completely arbitrary and an excuse to talk about songs I like.
So, in the order I thought of them, my top 100 songs, 5 at a time:
1. "Caught Up in You" by .38 Special (1982)
This hit from the extremely average looking .38 Special (when they still had punctuation) is an example of the perfect rock song. Perfect short intro, perfect verse length, perfect chorus with catchy enough melody to cover mistaken words, a perfect guitar solo (harmonizing guitar!), but most of all, a perfect bridge. This song may feature my favorite bridge from any song ever (at 2:13 and 2:53). I love the way they break it down with the unison rhythm of the instruments. I just love it too much!
Although the awkward flirting going on in this video dampens the song's effect a bit.
2. "I Want it That Way" by The Backstreet Boys (1999)
In the boy band war of the late 90s, I was staunchly a BSB fan (better music and better singers, duh). Their iconic song "I Want it That Way" is my favorite of their songs, and stands as a perfect example of how successful incomprehensible lyrics set to a catchy melody can be (the alternate version of the lyrics just sounds weird). Plus, it featured the voices of every one of the boys at some point in the song, including my beloved Kevin at the bridge of the song (of course).
'99 was also the summer I watched a ton of TRL. Worth it.
3. "I Can't Make You Love Me" by Bonnie Raitt (1991)
Best song if you're in the mood for a good cry. 'nuff said.
I have nothing to add.
4. "When the Levee Breaks" by Led Zeppelin (1971)
Led Zep at their grittiest. The drums are monstrous, the vocals are strong, the harmonica and slide guitar bring the sound out west while the guitar is a steady onslaught of awesome. It never feels like a 7 minute no matter how many times I hear it.
Great song to work custodial to, FYI.
5. "Baba O'Riley" by The Who (1971)
Also proving that long doesn't mean boring is the Who. There's such a perfect build to the song that gets more and more urgent as the song goes on, finally ending on a fast folk rhythm. And they use synthesizer so well that it sounds organic in the song. Seriously, a violin/synth duet? Brilliant.
Their live version with a harmonica is pretty great, too.
There's a reason these were the first 5 I thought of when making this list. From here on out the choices get increasingly more random. Until next time.