In the book River’s Edge: The Weezer Story, Ric Ocasek says that Rivers Cuomo was reluctant to include the song on the album:

I remember at one point he was hesitant to do ‘Buddy Holly,’ and I was like, ‘Rivers, we can talk about it. Do it anyway, and if you don’t like it when it’s done, we won’t use it. But I think you should try. You did write it and it is a great song.’

Matt Sharp added:

Ric said we’d be stupid to leave it off the album. We’d come into the studio in the morning and find little pieces of paper with doodles on them: WE WANT BUDDY HOLLY.

In an interview with Billboard on the 25th anniversary of The Blue Album, Patrick Wilson shares his view on the song:

It’s such a tightly written song. There’s no fat on it all. It starts at ten, and goes up from there. Ric Ocasek insisted that we put in on the album. I think that song was a little problematic for Rivers, because I think he wanted things to go in a certain direction. So when that song got big – partly because of a pretty important video – I think he thought the focus wasn’t on the right thing.
At the time, the very idea that you could watch a video on a computer was like madness! I remember being really mad at Geffen Records for putting that video on Windows 95 because I didn’t understand how promotion worked. But I came to find out that it was basically one of the biggest coups of all time. I’m an idiot, basically.

Yes, “Buddy Holly” was certified gold by the RIAA on February 15, 2006.

The “Buddy Holly” video won four awards at the 1995 MTV Video Music Awards, including prizes for Breakthrough Video and Best Alternative Video.