With Kendrick Lamar’s Damn facing off against Jay Z’s 4:44 for Album of the Year, 2018 could have been remembered as the one where rap finally broke through the Grammy Awards. However, Bruno Mars officially got the win. A hip-hop album hasn’t won since Outkast pulled it off way back in 2003. But what about past winners of Album of the Year? Which albums totally held up – and which ones didn’t? In order to make our list of the worst album of the year winners, the winner didn’t need to make a bad album. To truly be the worst, there needs to be a transcendent album on the losing side.

Frank Sinatra – A Man and His Music

The year 1967 conjures up images of great social change. The Civil Rights Movement was in full swing. America was at War in Vietnam. Woodstock was just two years away. Music was in the midst of a complete revolution, led by the British invasion and The Beatles. Guess who won the Grammy for Album of the Year in 1967? Frank Sinatra. The Chairman of the Board had already won the award twice, and his album, The Man and His Music, was just a compilation of previously recorded tunes. The Grammy voters were still stodgy though, overlooking one of the top 3 albums of all time: The Beatles’ Revolver.

Herbie Hancock – River: The Joni Letters

Herbie Hancock won Album of the Year in 2008. Yes, the jazz vocalist best known for the 1980’s hit “Don’t Worry, Be Happy,” somehow managed to win a Grammy in the 21st century for an album that only Grammy voters actually heard. Nobody even remembers it, but the two albums it beat out, Amy Winehouse’s Back to Black and Kanye West’s Graduation, inspired generations of musicians and still sound fresh today.

Steely Dan – Two Against Nature

In 2001, Grammy voters committed a crime against humanity by rewarding oldsters Steely Dan for their album Two Against Nature, which couldn’t even muster up radio play on classic rock stations, which trade in nostalgia, not new albums by old (very old) favorites. The Grammy voters compared it with Radiohead’s groundbreaking album Kid A and thought it was the superior music. The other choice that year could have been Eminem’s Marshall Mathers LP, which probably terrified Grammy voters.

Various Artists – Oh, Brother Where Art Thou? Soundtrack

My first thought about this win was literally, “what?” I mean, the movie was good and this is a nice album, full of excellent producing courtesy of the legendary T Bone Burnett. But it was 2001, Grammy voters need to reward the music of the time, not music that is literally out of time, don’t they? (Probably not) This polarizing win came at the expense of Outkast’s Stankonia.

Ray Charles and Various Artists – Genius Loves Company

Grammy voters proved yet again that they hate 21st century music in 2005. That year they bestowed another career achievement award in disgusting, giving a compilation album the award. The album was flush with big names and was released a few months after Charles died. However, two seminal albums vied for the trophy that year: Kanye West’s College Dropout and Green Day’s American Idiot. Both albums put a unique stamp on what it meant to be making music in America in the new century.

Christopher Cross – Christopher Cross

You can’t dispute that Christopher Cross’ debut album wasn’t a big hit. It dominated radio in 1981. The Grammy voters bestowed Cross with five awards for his soft-rock album of hits. However, two incredible albums walked away with nothing. Pink Floyd’s The Wall is still being played on college campuses everywhere. The Clash’s London Calling punctuated the era of punk rock, but it didn’t even garner a nomination.

Robert Plant & Alison Krauss – Raising Sand

In 2009, Grammy voters loved this album. It was by an artist they love (Alison Krauss) and one they hated and ignored when he was in an influential rock band (Led Zeppelin). Robert Plant is a singular singer, but this was a fairly pedestrian, defanged effort. Of course it beat out Radiohead’s In Rainbows, proving that Radiohead should finally get the win in 20 more years, when they do an unplugged banjo album.