I am a Blue Album person. And in fact I didn't own or listen to Pinkerton until well into the 2000s. I enjoyed El Scorcho as a single very well, but had kind of moved on from the mid-90s alt rock connecter piece between grunge and pop punk by the time Weezer released Pinkerton.
I feel like Pinkerton enjoyed a renaissance during the early-mid 2000s after the Green Album was released. And by this time, I was ready for Weezer again. I loved Green and decided to give Pinkerton (should be called Pink for short) a shot.
For a minute, Pinkerton displaced Blue as my favorite (the ranking has since self-corrected). Is this common? For a while, I thought that Pinkerton was the more common choice but then in 2010 Weezer did that thing where the fans voted on a Blue or Pinkerton tour and Blue buried Pink. I was surprised. Pitchfork wrote about Pink: "The album that killed Weezer's career ended up saving it." This was also in 2010, which I think was true from a Pitchforky perspective at the time. Today it's like "The album that killed Weezer's career saved it and then aged in a very, very troubling way."
Yeah, Pink is an uncomfortable listen. But "Why Bother?" is as good as ever. My clearest memory of enjoying this song was in 2004-05 or so. It was a random (possibly week-) night at Andyman's Treehouse in Columbus during the stretch when we practically lived there. This was because we were playing there a lot but also because it was during the time in our life when we could just hang out until 2 at a bar on a weeknight due to tenuous employment and--idk--a sense of invincibility? Someone put this song on and everyone in the crowded bar sang it at the top of their lungs. Looking back, this is a top-five defining moment of this era, along with staying up all night so that Gretchen could take Pete and I to the airport for an early flight home the following day and drinking Bomb Pops with Pete, Shaun, and Tonya to oblivion on the 4th of July.