The Grammy Legend Award, or the Grammy Living Legend Award, is a special award of merit given to recording artists by the Grammy Awards, a ceremony that was established in 1958 and originally called the Gramophone Awards. Honors in several categories are presented at the ceremony annually by the National Academy of Recording Arts and Sciences of the United States for outstanding achievements in the music industry.

The first Grammy Legend Awards were issued in 1990 to Andrew Lloyd Webber, Liza Minnelli, Smokey Robinson and Willie Nelson. The honor was inaugurated to recognize "ongoing contributions and influence in the recording field". The next year four more musicians (Aretha Franklin, Billy Joel, Johnny Cash and Quincy Jones) were acknowledged with Grammy Legend Awards. The award was given to Barbra Streisand in 1992 and Michael Jackson in 1993.

After 1994, when the American musicians Curtis Mayfield and Frank Sinatra were both issued Grammy Legend Awards, the honors have been given to recording artists intermittently. Italian operatic tenor Luciano Pavarotti was the 1998 recipient of the award. The following year, British singer-songwriter Elton John was recognized with the honor. The Bee Gees became the first recipients of the award in the 21st century when the brothers were acknowledged by the Grammys in 2003. Overall, fourteen solo musicians and one band have received the Grammy Legend Award.

Michael Joseph Jackson (August 29, 1958 – June 25, 2009) was an American recording artist, entertainer, and businessman. Often referred to as the King of Pop, or by his initials MJ, Jackson is recognized as the most successful entertainer of all time by Guinness World Records. His contribution to music, dance, and fashion, along with a much-publicized personal life, made him a global figure in popular culture for over four decades. The seventh child of the Jackson family, he debuted on the professional music scene along with his brothers as a member of The Jackson 5 in 1964, and began his solo career in 1971.

In the early 1980s, Jackson became a dominant figure in popular music. The music videos for his songs, including those of "Beat It", "Billie Jean", and "Thriller", were credited with transforming the medium into an art form and a promotional tool, and the popularity of these videos helped to bring the relatively new television channel MTV to fame. Videos such as "Black or White" and "Scream" made him a staple on MTV in the 1990s. Through stage performances and music videos, Jackson popularized a number of complicated dance techniques, such as the robot and the moonwalk, to which he gave the name. His distinctive musical sound and vocal style influenced numerous hip hop, post-disco, contemporary R&B, pop and rock artists.

William "Smokey" Robinson, Jr. (born February 19, 1940) is an American R&B singer-songwriter, record producer, and former record executive. Robinson is most notable for being the founder and front man of the popular Motown vocal group, The Miracles, for which he also served as the group's chief songwriter and producer. Robinson led the group from its 1955 origins as The Five Chimes until 1972 when he announced a retirement from the stage to focus on his role as Motown's vice president.

However, Robinson returned to the music industry as a solo artist the following year, later having solo hits such as "Baby That's Backatcha", "Quiet Storm", "The Agony and the Ecstasy", "Cruisin'", "Being With You" and "Just to See Her". Following the sale of Motown Records in 1988, Robinson left Motown in 1990. He was inducted into the Rock and Roll Hall of Fame in 1987.

Robinson was born in Detroit and raised in the city's North End section. At one point, he and Diana Ross were next-door neighbors; he said he has known Ross since she was eight. Robinson later told reporters when he was a child, his uncle christened him "Smokey Joe", which Robinson assumed was a "cowboy name for me" until he was later told that smokey was a pejorative term for dark-skinned Blacks. Robinson, who is mainly of African American descent and is light-skinned, remembers his uncle saying to him, "I'm doing this so you won't ever forget that you're black." Robinson grew up as a fan of Western films.

Janet Damita Jo Jackson (born May 16, 1966) is an American recording artist and actress. Known for a series of sonically innovative, socially conscious and sexually provocative records, as well as elaborate stage shows, television and film roles, she has been a prominent figure in popular culture for over 25 years. The youngest child of the Jackson family, she began her career with the variety television series The Jacksons in 1976 and went on to appear in other television shows throughout the 1970s and early 1980s, including Good Times and Fame.

After signing a recording contract with A&M in 1982, she came to prominence following the release of her third studio album Control (1986). Her collaborations with record producers Jimmy Jam and Terry Lewis incorporated elements of rhythm and blues, funk, disco, rap, and industrial beats, which led to crossover appeal in popular music. In addition to receiving recognition for the innovation in her records, choreography, music videos, and prominence on radio airplay and MTV, she was acknowledged as a role model for her socially conscious lyrics.

The Bee Gees were a musical group founded in 1958. The group's line-up consisted of brothers Barry, Robin, and Maurice Gibb. The trio were successful for most of their decades of recording music, but they had two distinct periods of exceptional success: as a pop act in the late 1960s/early 1970s, and as prominent performers of the disco music era in the late 1970s.

The group sang three-part tight harmonies that were instantly recognisable; Robin's clear vibrato lead was a hallmark of their earlier hits, while Barry's R&B falsetto became their signature sound during the late 1970s and 1980s. The brothers wrote all of their own hits, as well as writing and producing several major hits for other artists.

Born in the Isle of Man to English parents, the Gibb brothers lived their first few years in Chorlton, Manchester, England, then moved in the late 1950s to Redcliffe, Queensland, Australia, where they began their musical careers. After achieving their first chart success in Australia with "Spicks and Specks" (their 12th single), they returned to the United Kingdom in January 1967 where producer Robert Stigwood began promoting them to a worldwide audience.