And not just any Frank Sinatra album—A Man and His Music, which features just three tracks specifically recorded for the project, topped arguably the greatest LP of the 1960s in the album of the year category.

A short-lived disco act over one of the most brilliant pop singer-songwriters ever? Come on, guys! The Cars and Toto, also nominated in the category that year, would have been more acceptable upsets in this one.

Much love to Lionel, “Hello” and “All Night Long (All Night),” but Can’t Slow Down is not better than Born In The U.S.A. or Purple Rain. It’s not even close, really.

In 1989, Metallica was supposed to have the Best Hard Rock/Metal Performance category locked down with …And Justice For All. Then Jethro Tull, who somehow snuck in despite not being a hard rock or metal group, took home the gold with Crest of a Knave. At least the album title was pretty metal!

Okay, so there were a LOT of white guys nominated for album of the year in 2001, but the wrong white guys clearly won. Steely Dan’s ho-hum Two Against Nature somehow beat out Radiohead’s groundbreaking Kid A, Eminem’s landmark The Marshall Mathers LP and Beck’s way-more-fun-than-you-remember Midnite Vultures.

Genius Loves Company, Ray Charles’ final release, was up against Green Day’s American Idiot, Usher’s Confessions, Kanye West’s The College Dropout and Alicia Keys’ The Diary of Alicia Keys for Album of the Year. Once again, sentimentality won out over good music (and G.O.O.D. Music).

Looking back, the 2011 Best New Artist class was stacked: Drake, Justin Bieber, Mumford & Sons and Florence + The Machine have all enjoyed remarkably successful careers since then. Still, none of them could top contemporary jazz artist Esperanza Spalding, who has gone on to carve a respected place in modern music without dominating radio.

If Eminem wasn’t going to win Album of the Year for Recovery, his third Album of the Year nomination, then Gaga was going to win it for The Fame Monster, her second Album of the Year nomination in a row. Instead, Canadian indie-rockers Arcade Fire strode onstage for The Suburbs—despite their third LP losing out in the Best Alternative Album category.

Ah, the infamous text-message category: Macklemore & Ryan Lewis’ The Heist topped Kendrick Lamar’s good kid, m.A.A.d city for Best Rap Album in 2014, and Macklemore decided to Mackle even more by shooting Kendrick an apologetic text… which he then posted on Instagram, and which went viral.

Beyoncé’s self-titled opus was a shoo-in to win Album of the Year… until it wasn’t, since Beck’s Morning Phase, a surprise nominee, became a shocking winner. Kanye West almost crashed the stage to interrupt Beck’s acceptance speech, as he did to Taylor Swift in 2009, but decided against it at the last minute.