As evidenced by Will Smith and Public Enemy’s boycotting of the 1989 Grammy Awards, mainstream awards shows haven’t always been best friends with the world of hip-hop. While we’ve come along way from the days when rappers weren’t even given the chance to accept trophies during the Super Bowl of music awards shows, every once in a while, the seemingly irreconcilable gap between the interests of “true” rap fans and awards committees rears its plain-faced to flat-out ugly head. 50 Cent knows firsthand the unpleasantness of a major awards show upset.

The rapper’s Get Rich or Die Tryin’ album earned widespread acclaim upon its release in 2003, and by the end of the year, it sold a gargantuan total of 12 million copies. Still, Fif found himself at the losing end of the competition for Best New Artist at the 2004 Grammys. That honor instead went to Evanescence, a group whose album Fallen earned mixed reviews and sold millions of copies less than Fif’s ubiquitous debut. Years later in 2011 Drake—who’d yet to become the all-consuming pop culture phenomenon he is today—suffered the same fate, losing to singer Esperanza Spalding in the same category.

Rappers losing out to artists in other genres is a sting to their fans, but most of the time, the hurt is even worse when they suffer an unexpected loss to a less critically acclaimed MC. Case in point, the 2014 Grammy Awards, where Macklemore and Ryan Lewis' The Heist bested Kendrick Lamar’s good kid, m.A.A.d city for Best Rap Album. While Macklemore’s breakthrough project had plenty of tracks that graced the Billboard Hot 100 chart, K. Dot’s major label debut was one of the most revered rap albums of the last 15 years.

Rap fans were more than a little upset about the Compton lyricist’s loss at the popular awards show, but that disappointment is basically par for course in the rap game. With that in mind, XXL takes a look at 10 instances in which hip-hop and its fans faced major upsets at big awards shows -- whether it's a rapper losing to a pop star or to one of their fellow MCs. Check out the unexpected L’s some of the genre’s most prominent names have taken throughout recent history.

  • 1

    Ol' Dirty Bastard Gets Angry When Diddy Wins Rap Album of the Year at 1998 Grammy Awards

    Ol' Dirty Bastard wasn’t too happy when the shiny suit-wearing Puff Daddy's No Way Out beat Wu-Tang Clan's Wu-Tang Forever for Best Rap Album at the 1998 Grammy Awards. Never one to hold his tongue, he made his feelings known to the awards committee when he crashed the stage just before singer Shawn Colvin could begin her acceptance speech for winning Song of the Year. Needless to say, it was more than a little awkward. Did ODB have a point? Fans who didn't respect Diddy's penmanship (or lack thereof) would say so. However, Puff's album didn't go seven times platinum for no reason, and "Victory," "All About the Benjamins (Remix)" and "I'll Be Missing You" have proven to be bangers for the ages.

  • 2

    50 Cent Loses to Evanescence for Best New Artist at 2004 Grammy Awards

    In 2004, 50 Cent was everywhere from blasting from headphones in the grimiest corners of New York to the radio in your friend’s cousin's living room. His debut album, Get Rich or Die Tryin’, was led by the single “In da Club,” which sprinted up the charts as soon as it was released -- in its first year, the LP sold 12 million copies. The album received nearly universal acclaim from music critics with songs like "21 Questions" and "P.I.M.P."  Still, Fif was no match for Evanescence, a rock group whose single “Bring Me to Life” was also one of the most popular songs of 2003. The then up-and-coming group ended up taking home the Grammy for Best New Artist in 2004. While Evanescence definitely had some fire of their own, 50 failing to win was an upset. The rapper was pretty much the biggest thing in music during 2004, and his record sales and critical acclaim prove it.

  • 3

    Drake Loses to Esperanza Spalding for Best New Artist at 2011 Grammy Awards

    Esperanza Spalding stunned just about everyone when she beat out Drake for Best New Artist at the 2011 Grammy Awards, and for good reason. On one hand, she released her debut album, Junjo, in 2006, almost five years before Drake dropped Thank Me Later in 2010, thus making the label "new artist" seem like a bit of a stretch. On the other, her win upset Drizzy, whose So Far Gone mixtape and debut album had already made him one of the music industry's biggest stars. While hip-hop took a hit when Drake took this loss, he was proved to be a winner when his second album, Take Care, won Best Rap Album at the 2013 Grammys.

  • 4

    Nicki Minaj Loses to Bon Iver for Best New Artist at 2012 Grammy Awards

    Nicki Minaj’s 2010 debut album, Pink Friday, immediately established her as the most commercially viable female rapper in hip-hop, while also laying the groundwork for her to be the crossover star she is today. Serving as a showcase for the animated Barbie’s dexterous flow, hard-hitting lyrics and the vocal chops of a bona fide pop star, Pink Friday was virtually guaranteed to earn the Young Money rapper a Grammy Nomination for Best New Artist in 2012. It did, but unfortunately for Nicki, the award ended up going to indie folk group Bon Iver. Fans noted that Nicki's immediate pop culture dominance should've won her the trophy, especially considering the fact that Bon Iver actually dropped their first album in 2007, four years prior to the awards show. We don't necessarily have a horse in this race, but it is sort of hard to be a new artist five years after you've released your first LP.

  • 5

    Lil Wayne Bests Drake, Kanye West & Jay Z at the 2012 Billboard Music Awards

    Don't get it twisted: Lil Wayne is one of the greatest rappers of all time. Still, his album, The Carter IV, was probably his most lackluster effort up to that point--at least in comparison to Jay Z and Kanye West's Watch the Throne or Weezy's protege Drake's Take Care. That didn't stop the project from beating those rap superstars out for Rap Album of the Year at the 2012 Billboard Music Awards. Take Care and Watch the Throne did similarly stellar numbers to the fourth installment in Weezy's The Carter series, but The Carter IV still bested both  -- even though Drizzy, Hov and 'Ye's efforts received significantly better reviews from music critics everywhere.

  • 6

    Iggy Azalea Wins Favorite Rap/Hip-Hop Artist at 2014 American Music Awards

    Iggy Azalea began what would be a stunningly successful awards show season by taking home the trophy for Favorite Rap/Hip-Hop Artist at the 2014 American Music Award, upsetting industry titans Drake and Eminem in the process. Her album, The New Classic, went platinum a few months after she won this award. While fans of the Australian rapper weren't losing any sleep over her W, more than a few fans weren't too pleased to see her victory at the AMAs. Iggy's perceived faux-Southern accent and pop sensibilities have made her a target for rap purists since she stepped into the rap game years ago. For them, Iggy's win over established superstars like Drake and Em was just another example of White rappers winning the prizes they think rightfully belong to Black artists.

  • 7

    Kendrick Lamar Loses to Macklemore for Best Rap Album at 2014 Grammy Awards

    Kendrick Lamar set the rap world ablaze with his debut album, good kid, m.A.A.d city, which not only went platinum in under a year’s time, but also earned acclaim from rap critics everywhere. With these accomplishments in mind, winning the Grammy for Best Rap Album seemed inevitable—until it wasn’t. Enter Macklemore, a White rapper whose feel-good, fearlessly suburban album, The Heist, managed the rare feat of going gold without the help of a major label. With the pop sensibilities of tracks like “Thrift Shop” and “Can’t Hold Us” making the Seattle artist a Billboard Hot 100 mainstay, it suddenly didn’t seem all that crazy that he could take home the award many people thought belonged to Kendrick. When the big night came, Macklemore’s project took home the trophy for Best Rap Album at the 2014 Grammys. Not too many folks were happy about this one, not even Macklemore himself. The “Same Love” performer sent an apologetic text to K. Dot shortly after his award win and uploaded a screenshot on their conversation to his Instagram account hours later. For his part, K. Dot wasn’t feeling Macklemore’s gesture.

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  • 8

    Iggy Azalea Wins Favorite Hip-Hop Artist at 2015 People's Choice Awards

    To be fair, this award is voted for by the fans. Still, many hip-hop fans were pretty surprised to see Iggy Azalea beat out Jay Z, Drizzy, Nicki Minaj and T.I. for Favorite Hip-Hop Artist at the 2015 People's Choice Awards. Those are pretty much the faces of hip-hop, so it's easy to see why people were shocked by her win--she was still something of an upstart. Iggy's first album, The New Classic, didn't get a ton of love from critics, but it did spawn a few chart-topping singles and establish the Australia native as a force in the rap game.

  • 9

    Meek Mill Wins Top Rap Album at 2016 Billboard Music Awards

    Kendrick Lamar's To Pimp a Butterfly won several Grammys in 2016, so it seemed like a foregone conclusion that he'd also take home the less notable, but still prestigious Billboard Award for Top Rap Album in 2016. Instead, Meek Mill's Dreams Worth More Than Money won the trophy, handing K. Dot one of the only L's he suffered that year. He also beat out Drizzy, who he famously outed for using a ghostwriter a year before. Revenge is sweet.

  • 10

    G-Eazy Wins Favorite Hip-Hop Artist at 2017 People's Choice Awards

    Over the last few years, G-Eazy has become one of the Bay Area's most accomplished MCs, and he solidified his status as a serious rap star with his 2015 album, When It's Dark Out. The project earned platinum status in under a year's time and helped the Cali rapper beat out Kanye West, Kendrick Lamar, Wiz Khalifa and DJ Khaled for Favorite Hip-Hop Artist at the 2017 People's Choice Awards.

    Although the "Me, Myself & I" performer had a great 2016, not too many people expected him to win the award over folks like Kendrick Lamar and Kanye West, two of the rap game's biggest stars. While G-Eazy's album did go platinum in six months, it was still hard for some fans to accept that he could be favored over his other more established contemporaries. A few fans let their feelings of disappointment be known online, but we have a feeling G-Eazy isn't too upset.