Robert Matthew Van Winkle, best known by his stage name Vanilla Ice, is an American rapper. Born in Dallas, Texas, and raised in Texas and South Florida, Van Winkle released his debut album, Hooked, in 1989 through Ichiban Records, before signing a contract with SBK Records, which released a reformatted version of the album under the title To the Extreme. Van Winkle's single "Ice Ice Baby" was the first hip hop single to top the Billboard charts.

Although Van Winkle was successful, he later regretted his business arrangements with SBK, which had paid him to adopt a more commercial appearance and had published fabricated biographical information without his knowledge. After surviving a suicide attempt by drug overdose, Van Winkle was inspired to change his musical style and lifestyle. Later albums by Van Winkle, including Hard to Swallow, Bi-Polar and Platinum Underground, had a less mainstream rock-oriented sound, and did not chart.

Robert Matthew Van Winkle was born on October 31, 1967 in Dallas, Texas. Van Winkle never knew his real father, and was given the name of the man his mother was married to at the time of his birth. Because of his parents' divorce, he grew up moving between Dallas, where he lived with his mother and stepfather, and Miami with his father. Van Winkle's stepfather was a car salesman. Between the ages of 13 and 14, Van Winkle practiced breakdancing, which led to his African American friends calling him "Vanilla Ice." Although he disliked the nickname, it stuck, and he began to rap as Vanilla Ice. Van Winkle wrote "Ice Ice Baby" at the age of 16, basing its lyrics upon his experiences in South Florida. The lyrics describe a drive-by shooting and praise Van Winkle's rhyming skills.

In 1987, Van Winkle met Tommy Quon at his Dallas night club City Lights. Upon seeing Van Winkle's performance, Quon saw commercial potential in his rapping and dancing skills, and offered him a contract with his management company, Ultrax. Van Winkle signed a contract with Ichiban Records in 1989, and released his debut album, Hooked." Play That Funky Music" was released as the album's first single, with "Ice Ice Baby" appearing as the B-side. When a disc jockey played "Ice Ice Baby" instead of the single's A-side, the song was more popular than "Play That Funky Music". Quon financed $8000 for the production of a music video for "Ice Ice Baby", which received heavy airplay by The Box, increasing public interest in the song. Van Winkle later opened for EPMD, Ice-T, Stetsasonic and Sir Mix-A-Lot on the Stop the Violence Tour.

Van Winkle's current live performances feature a mix of newer, rock-influenced material and old school hip hop. Van Winkle performs with a live drummer and DJ, and sometimes sprays his audience with bottled water. Van Winkle's performances often feature an inflatable grim reaper balloon, a dancer in a clown mask, and confetti thrown into the audience. Describing his performances, Van Winkle stated "It's high energy, stage diving, pyrotechnics, girls showing their breasts. It's crazy party atmosphere."

Van Winkle stated that his musical style was influenced by underground music, rather than mainstream music, and that his influences included hip hop and funk artists such as Funkadelic, Rick James and Parliament. Van Winkle also stated that he enjoys Rage Against the Machine, Slipknot and System of a Down. Van Winkle sometimes plays bass, drums and keyboards on studio recordings. Rapper G-Child, best known for her appearance on ego trip's The (White) Rapper Show, has credited Van Winkle as being a major influence on her work. After meeting Van Winkle in 2000, G-Child performed freestyle raps at six of Van Winkle's performances, and opened for him four times.

Along with Beastie Boys, 3rd Bass and House of Pain, Van Winkle was one of the earliest white rappers to attain major success. Chuck D has credited Van Winkle as a regional breakthrough, stating "He broke through in the mid-south, in a southern area in Texas, in something that was kind of indigenous to that hip-hop culture down there. He just doesn’t get credit for it." As a result of his success, Van Winkle was the subject of criticism from other hip hop musicians. In 1991, 3rd Bass released a single called "Pop Goes the Weasel", and in the lyrics comparing Van Winkle unfavorably to Elvis Presley. The song's music video featured Henry Rollins as Van Winkle, who is depicted as being assaulted by 3rd Bass. Del tha Funkee Homosapien referred to Van Winkle as mocking hip hop in the lyrics of "Pissin' on Your Steps", which appeared on his 1991 debut album I Wish My Brother George Was Here.

In March 2009, Van Winkle participated in a Virgin Mobile advertising campaign titled "Right Music Wrongs", apologizing for his 1990s image. As part of the campaign, Van Winkle was placed on "trial", and was voted innocent by users of the campaign website. He also appeared in a commercial for the South African light beer Castle Lite. In 2010, Vanilla Ice was featured on the debut single of the Irish duo John & Edward, a mashup of "Under Pressure" and "Ice Ice Baby". "Under Pressure (Ice Ice Baby)" was released in the United Kingdom on January 31, 2010 via download and as a physical single on February 15, 2010.