It didn’t take long for Lou Reed to outgrow the Beach Boys cash-ins he was making as a contract artist and songwriter and head toward more fertile land. By 1965, he had met John Cale, and the pair started working on the music that would become the core foundation of the Velvet Underground. Within two years, they released one of the most influential albums ever recorded.

Still, it was a rocky start and rarely a lucrative one. From his early doo-wop fixations to a long career filled with band, solo and collaboration records that were confrontational, purposely difficult and designed outright for commercial failure, Reed never compromised, as you’ll note in the list below of Lou Reed and the Velvet Underground Albums Ranked.

The four albums he made with the Velvet Underground – before he walked away in disgust at the band’s lack of success – are acknowledged classics today, but they were commercial bombs when they were released. His solo album Transformer gained him Top 40 fame in 1972; it wasn’t long before Reed undermined his career with albums like Berlin (a concept album about addiction and suicide) and Metal Machine Music (often cited as one of the worst albums of all time).

READ MORE: How Loud Reed Made One of Rock’s Most Hated Albums

Reed was an uncompromising artist until he died in 2013. His final album, Lulu, a collaborative LP with Metallica, received backlash from fans of both artists and frequently appears alongside Metal Machine Music on lists of the worst albums ever made. There aren’t too many people who’ve made one of the most influential records ever and one (or two) of the most reviled.

The list of Lou Reed and the Velvet Underground Albums Ranked Worst to Best includes only studio albums, but a couple of live releases, both from 1974, are essential listens: Reed’s Rock n Roll Animal, which features four Underground songs and one from Berlin, and the Velvets’ 1969: Velvet Underground Live With Lou Reed, which cherry-picks songs from a pair of shows in Dallas and San Francisco. They help tell the story of one of music’s most unwavering and contentious figures.