U2 Winning Album of the Year Over Michael Jackson, Prince, Whitney Houston, 1988

Album of the Year is the biggest category at each Grammy Award show. In 1988, three of the biggest acts in the world were nominated for the award; Michael Jackson’s Bad, Prince’s Sign O’ the Times, and Whitney Houston’s Whitney. And the winner was…U2. The Irish rock quartet won for their hit album, The Joshua Tree.

Prince would tell Rolling Stone two years later, “I’m not saying I’m better than anybody else. But you’ll be sitting there at the Grammys, and U2 will beat you. And you say to yourself, ‘Wait a minute. I can play that kind of music, too… But you will not do ‘Housequake.'”

The 1989 Rap Category Boycott

The world didn’t know what to make of rap music when it burst onto the scene. Neither did The Recording Academy. When Run DMC was nominated for “Walk This Way,” it was for R&B Performance by a Duo or Group. In 1989, a rap category was finally added to the Grammys but it was not part of the televised broadcast.

As a result, members of the hip-hop community, including LL Cool J, Russell Simmons, Salt-N-Pepa, and DJ Jazzy Jeff & The Fresh Prince staged a boycott of the ceremony. They felt being excluded from the telecast was “disrespectful,” while Jeff added that rap’s popularity warranted its presence. “They televised 16 categories and, from record sales, from the Billboard charts, from the overall public’s view, there’s no way you can tell me that out of 16 categories, that rap isn’t in the top 16,” Jeff said.

India.Arie Goes Home Empty-Handed in 2002

India Arie was riding high with her 2001 debut album, Acoustic Soul. With its introspective themes, empowering lyrics, and dynamic, catchy melodies, Arie earned seven Grammy nominations in 2002. Unfortunately, she went head to head with fellow R&B singer/songwriter Alicia Keys in five different categories. Keys won them all, and Arie lost her remaining two; Album of the Year, and Record of the Year.

Perhaps as a make-good, the Recording Academy created the Best Urban/Alternative Performance category the following year. Arie did win in the new category for “Little Things” from her album Voyage to India, but the damage had already been done. She told Oprah Winfrey years later that on the night she lost, she felt maybe she didn’t “deserve” to win.

Macklemore & Ryan Lewis ‘Heist’ Vs. Kendrick Lamar in 2014

Kendrick Lamar was poised to have a coming-out party at the 2014 Grammys. That year, the Compton rapper received seven nominations, including Album of the Year, for his sophomore release, the critically-acclaimed concept album, good kid, m.A.A.d. city. That was the same year that Washington state rap duo Macklemore & Ryan Lewis hit it big with their hit, “Thrift Shop” from their album, The Heist.

Turns out that The Heist was a fateful title. Not only did Lamar end the night with zero wins, but Macklemore and Lewis beat him in four categories, including Best New Artist, Best Rap Album, Best Rap Performance, and Best Rap Song. Lamar said on 97.1 FM’s Ebro in the Morning later that Macklemore texted him afterward, saying he wished Lamar had won instead.

Last-Minute Maurice White Tribute, 2016

The 2016 Grammys featured several tributes to recently departed artists. The ceremony featured all-star tributes to David Bowie, Eagles guitarist Glenn Frey, and Motörhead bassist/frontman, Lemmy, who all died within two months of the Grammys. Unfortunately, their tribute to Earth, Wind & Fire founder Maurice White, who died weeks after Bowie, seemed like an afterthought judging by its execution.

White’s tribute was done at the podium as part of an award presentation, rather than on the main stage. Stevie Wonder and acapella group Pentatonix sang one line from Earth, Wind & Fire’s “That’s the Way of the World,” before presenting the Song of the Year trophy. The tribute seemed thrown together, and disrespectful to White, who had more career Grammy wins (7), than Bowie (5), Frey (6), and Lemmy (1).