It all started way back at the inaugural Grammy Awards in 1959, when musical icons like Frank Sinatra, Ella Fitzgerald and Sammy Davis, Jr. were nominated in various categories. Despite having six nominations, Ol' Blue Eyes walked away with only the award for best art director for his "Only the Lonely" album cover. Meanwhile Domenico Modugno took home the prestigious Record of the Year and Song of the Year for "Volare" [source: Grammy].
Thus, began a rich history of the Grammys giving awards to artists who would eventually be far outpaced by their category competitors. In 1973, the band America beat out the Eagles for the 1972 Grammy of best new artist, and the same thing happened to Led freakin' Zeppelin in 1970 when they lost the prize to Crosby, Stills & Nash. To be fair, the latter did go on to become fairly influential, but are considered by many to be a mere shadow of Led Zeppelin. Crooner Marc Cohn, who scored exactly one hit ("Walking in Memphis"), won the same category in 1992 against uber-successful R&B group Boyz II Men [source: Whittaker].
More damaging, the rap-pop duo Milli Vanilli's 1990 best new artist award was vacated when everyone found out that neither group member actually sang on their album — other uncredited folks did the heavy lifting [source: Los Angeles Times staff]. Also in the inexplicable category: At the 31st Annual Grammy Awards (held in 1989) Jethro Tull and their decidedly un-metal album ("Crest of a Knave" heavily featured the flute) defeating Metallica's "And Justice For All" in the first-ever hard rock/heavy metal category. This was a real head-scratcher that metalheads found downright insulting [source: TIME]. As fired up as these missteps made some viewers, they also kept them watching, talking and nowadays, tweeting.
The rap music genre was also a big source of Grammy-associated controversy. It wasn't until 1989 that the Grammys finally saw the addition of a rap category to the mix, bringing great joy and validation to the artists who'd worked tirelessly to establish it. But the slap in the face came later when the nominees found out that the relevant award(s) wouldn't be televised, and instead would be presented as part of the ceremony earlier in the day. As a result, major names in rap, like Russell Simmons, Will Smith (then known as The Fresh Prince) and Public Enemy boycotted the ceremony outright, choosing instead to hold a press conference calling out the organization. The powers that be paid attention, and rap got its due the next year, when the award was televised [source: Coscarelli].
Fast-forward a bit, and although the Grammys have wised up to the staying-power and influence of rap, the category continues to generate some unpleasant buzz. In 1992 DJ Jazzy Jeff & The Fresh Prince took the Grammy for Best Rap Performance by a Duo or Group over Public Enemy's wildly popular, acclaimed and controversial "Apocalypse 91 – The Enemy Strikes Back." And the 56th Annual Grammys in 2014 saw white rappers Macklemore & Lewis (who some rap fans don't consider "real rappers") sweep three of the four major rap categories, shutting out the critically lauded Kendrick Lamar.
The outcry following this major snub was swift and real, and Lamar was awarded two trophies the next year. But recognition was truly to be his two years later, when his album "To Pimp a Butterfly" was nominated for a record-breaking 11 awards. Although he didn't win either of the two major general categories he was nominated for, he did take all four rap trophies [source: Rys].