From Rolling Stone:
In the early 1990s, Cuomo had an awkward girlfriend who was routinely picked on. His efforts to stick up for her inspired Weezer’s breakthrough, a track whose bubble-grunge hooks and lines such as “I look just like Buddy Holly/And you’re Mary Tyler Moore” helped the band reach a nation of pop-minded suburban punks. It also earned them personalized, autographed photos from the real Mary Tyler Moore.
The single was released on what would have been Buddy Holly’s 58th birthday, had he not been killed in a plane crash along with fellow rock pioneers Ritchie Valens and The Big Bopper on February 3, 1959.
Rivers Cuomo has stated in one of his MySpace blogs from 2006 that he remembers questioning whether or not to include this song on The Blue Album. He almost kept it off the final track list, but encouragement from producer Ric Ocasek soon changed his mind. In the book River’s Edge, Ocasek is quoted as saying, “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.'” Cuomo said that he felt the song was “too cheesy” and didn’t know if the song represented the sound he was going for with the band’s music. Matt Sharp recalls: “…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.”
From AbsolutePunk, reviewing the album:
The band’s claim to fame were the three singles released from the record: “Undone – The Sweater Song,” “Buddy Holly” and “Say It Ain’t So.” Occasionally, the infectious, pop-punk catchiness of the former two singles was overlooked, due to the critical acclaim of the Spike Jonze directed music videos, which won both Jonze and the band many awards.
…Weezer always accompany the songs with catchy guitar hooks and clever lyrics by Cuomo, and well harmonized vocals, courtesy of Brian Bell and Matt Sharp.
From the Wikipedia entry on the album:
While prepping for the forthcoming studio sessions, the band focused on their vocal interplay by practicing barbershop quartet-styled songs, which helped both Rivers Cuomo and Matt Sharp achieve a newfound collaborative comfort during rehearsals. Sharp, who never sang before joining Weezer, got his falsetto background vocal abilities — “I had to sing an octave higher than Rivers. After a lot of practice, I started to get it down.”
The band briefly considered self-producing, but were pressured by Geffen to choose a producer. They ultimately decided on Ric Ocasek. Cuomo: “I’d always admire The Cars and Ric Ocasek’s songwriting and production skills.” During production, Ocasek convinced the band to change their guitar pickup from the neck pick-up to the bridge pick-up, resulting in a brighter sound.
During these sessions, founding guitarist Jason Cropper left the band and was replaced by current guitarist Brian Bell, leading to some speculation about how much Bell contributes to the album. While Bell’s vocals are clearly audible…, frontman Rivers Cuomo re-recorded all of Cropper’s guitar parts.
From allmusic, reviewing the album:
Even if you lived through it, it’s hard to fathom exactly why Weezer were disliked, even loathed, when they released their debut album in the spring of 1994. If you grew up in the years after the heyday of grunge, it may even seem absurd that the band were considered poseurs, hair metal refugees passing themselves off as alt-rock by adapting a few tricks from the Pixies and Nirvana songbooks and sold to MTV with stylish videos. Nevertheless, during alt-rock’s heyday of 1994, Weezer was second only to Stone Temple Pilots as an object of scorn, bashed by the rock critics and hipsters alike. Time has a way of healing, even erasing, all wounds, and time has been nothing but kind to Weezer’s eponymous debut album (which would later be dubbed The Blue Album, due to the blue background of the cover art). At the time of its release, the group’s influences were discussed endlessly — the dynamics of the Pixies, the polished production reminiscent of Nevermind, the willful outsider vibe borrowed from indie rock — but few noted how the group, under the direction of singer/songwriter Rivers Cuomo, synthesized alt-rock with a strong ’70s trash-rock predilection and an unwitting gift for power pop, resulting in something quite distinctive. Although the group wears its influences on its sleeve, Weezer pulls it together in a strikingly original fashion, thanks to Cuomo‘s urgent melodicism, a fondness for heavy, heavy guitars, a sly sense of humor, and damaged vulnerability, all driven home at a maximum volume. While contemporaries like Pavement were willfully, even gleefully obscure, and skewed toward a more selective audience, Weezer’s insecurities were laid bare, and the band’s pop culture obsessions tended to be universal, not exclusive. Plus, Cuomo wrote killer hooks and had a band that rocked hard — albeit in an uptight, nerdy fashion — winding up with direct, immediate music that connects on more than one level. It’s both clever and vulnerable, but those sensibilities are hidden beneath the loud guitars and catchy hooks. That’s why the band had hits with this album — and not just hits, but era-defining singles like…the postironic love song of “Buddy Holly”… — but could still seem like a cult band to the dedicated fans; it sounded like the group was speaking to an in-crowd, not the mass audience it wound up with.