Pop music is a fickle mistress, and it's never certain exactly what will please whatever deity is in charge of who becomes a big deal and who doesn't. Back in 1992, things got really weird for Evan Dando, the frontman and primary songwriter for a ragtag little indie rock trio called the Lemonheads. They had gained a little bit of steam in the college rock community with four albums and a handful of EPs of shambling, workmanlike jangle pop. Then on this day in 1992, they released their fifth album It's a Shame About Ray, and everything got a little bit cagey.

Shortly after the release of It's a Shame About Ray, Dando and his band recorded a cover version of Simon and Garfunkel's "Mrs. Robinson" and released it as a single. It quickly became a huge hit on modern rock radio. Though it wasn't included on the original pressing, "Mrs. Robinson" ended up tacked onto re-released versions of It's a Shame About Ray. It became a mixed blessing for Dando, as the success of the song provided the band with more attention and adoration than they had ever had, but that all happened on the back of a cover song (which he quickly grew tired of).

Still, It's a Shame About Ray remains a gorgeously understated album full of lovely, exacting songwriting, charmingly shabby playing and Dando's sharp, sad lyrics. Though they were deeply personal, Dando infused his songs with a penetrating universality: "My Drug Buddy" was instantly recognizable to anybody who ever saw a relationship spiral out of control, and "Alison's Starting to Happen" became a coming-of-age anthem for girls looking to express themselves. But the highlight of the album is the title track, which let's Dando's slack-jawed croon ride a hazy, breezy riff. It's all about sadness and danger, which is a pretty good set of descriptors for 1992.

And yes, that is Johnny Depp in the video.

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