Bob Dylan, the most respected songwriter of the rock era, has never been nominated for Song of the Year. (The Grammys were averse to rock when he wrote many of his most classic works, including "Blowin' In The Wind.")
The Beatles never won for Record of the Year, despite nominations for four all-time classics—"I Want To Hold Your Hand," "Yesterday," "Hey Jude" and "Let It Be." The Fab Four did win in the other top Grammy categories—Album of the Year (for "Sgt. Pepper's Lonely Hearts Club Band"), Song of the Year (for "Michelle") and Best New Artist.
The Rolling Stones weren't nominated for a Grammy in any category until 1978, when "Some Girls" was a finalist for Album of the Year. In 1986, the Recording Academy made amends by bestowing a Lifetime Achievement Award upon the band. The Stones finally won their first two Grammys in 1995—more than 30 years after their U.S. breakthrough.
Pink Floyd's 1973 classic "The Dark Side Of The Moon," which has spent a record 852 weeks on The Billboard 200, was nominated in just one category—Best Engineered Recording, Non-Classical. The Academy seems to realize it goofed: The album was voted into the Grammy Hall of Fame in 1999.
Polka king Jimmy Sturr has amassed as many Grammys as soul queen Aretha Franklin. Both artists have won 18 awards.
Diana Ross has never won a Grammy, either on her own or with the Supremes. In 2012, the Academy presented the diva with a Lifetime Achievement Award.
Reggae legend Bob Marley never won a Grammy. The Grammys didn't add a reggae category until 1984, three years after Marley died of cancer. In 2001, the Academy voted Marley a posthumous Lifetime Achievement Award.
Lauryn Hill won two Grammys (as a member of the hip-hop trio Fugees) two years before she was crowned Best New Artist of 1998. Eligibility rules have since been tightened so that new artists have to be, well, new.
"Bill Clinton, Mikhail Gorbachev & Sophia Loren" sounds like the set-up to a really corny joke, but these three Very Famous People shared a Grammy for Best Spoken Word Album for Children for 2003's "Peter And The Wolf"/"Wolf Tracks."
Country star LeAnn Rimes was just 14-1/2 in February 1997 when she won two Grammys, including Best New Artist. She remains the youngest artist to win a Grammy. Despite that fast start, she hasn't won another Grammy since that night.
Christopher Cross is the only artist to sweep the Big Four awards—Record, Album and Song of the Year and Best New Artist—in one night. Alas, it was a case of too much, too soon. Cross hasn't won another Grammy since that unforgettable night.
Kanye West has won 21 Grammys, more than The Beatles, Barbra Streisand and James Taylor combined. But he's still not content. Twenty of West's Grammys have come in the rap field; the other in the R&B field (for co-writing an Alicia Keys hit). West wants to win in a Big Four category. Is he being a sore winner or does he have a point? You decide.