Who dated Vanilla Ice?

Robert Matthew Van Winkle (born October 31, 1967), known professionally as Vanilla Ice, is an American rapper, singer, actor, and television host. Born in Dallas and raised in Miami, he was the first solo white rapper to achieve commercial success, following the 1990 release of his best-known hit "Ice Ice Baby". He is credited with breaking down racial barriers in rap and hip-hop for future white rappers, most notably Eminem.

Ice released his debut album, Hooked, on the independent Ichiban Records before signing a contract with SBK Records, a record label of the EMI Group, which released a reformatted version under the title To the Extreme; it became the fastest-selling hip hop album of all time and "Ice Ice Baby" was the first hip hop single to top the Billboard Hot 100. Followed by the live album Extremely Live (1991), Ice made a cameo appearance on the film Teenage Mutant Ninja Turtles II: The Secret of the Ooze (1991) where he performed "Ninja Rap", which he co-wrote. He was soon offered and starred in his own film, Cool as Ice (1991), which included the single "Cool as Ice (Everybody Get Loose)" with Naomi Campbell; the film itself was a box office failure.

His fast rise in popularity was quickly marred by media controversies about his background. Ice later regretted his business arrangements with SBK, who had also published fabricated biographical information without his knowledge. Ice's second studio album, Mind Blowin' (1994), featured a major image change but was commercially unsuccessful. Following rap rock performances in the underground scene and playing in a local grunge band, Ice released the dark nu metal album Hard to Swallow (1998), followed by the independently released Bi-Polar (2001) and Platinum Underground (2005).

In the 2000s, Ice began appearing on television reality shows including The Surreal Life. In 2010, Ice began hosting The Vanilla Ice Project on DIY Network which ran for nine seasons until 2019. In 2022, he started another home improvement television program, The Vanilla Ice Home Show. He is also involved in motocross racing and real estate.

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Madonna Louise Ciccone ( chih-KOH-nee; born August 16, 1958) is an American singer, songwriter, record producer, and actress. Dubbed the "Queen of Pop", she is known for her continual reinvention and versatility in music production, songwriting, and visual presentation. Her works, which concern social, political, sexual, and religious themes, have generated both controversy and critical acclaim. Regarded as one of the most influential musicians of all time, Madonna broke gender barriers in popular music and has had a significant socio-cultural impact across her career.

Born and raised in Michigan, Madonna moved to New York City in 1978 to pursue a career in dance. After performing as a drummer, guitarist, and vocalist in the rock bands Breakfast Club and Emmy, she rose to stardom with her debut studio album, Madonna (1983). She has scored eighteen multi-platinum albums globally, including Like a Virgin (1984), True Blue (1986), and The Immaculate Collection (1990)—some of the best-selling albums of all time—and Confessions on a Dance Floor (2005), her 21st-century bestseller. Like a Prayer (1989), Ray of Light (1998), and Music (2000) were ranked among Rolling Stone's greatest albums of all time. Madonna's top-charting singles include "Like a Virgin", "Papa Don't Preach", "La Isla Bonita", "Like a Prayer", "Vogue", "Take a Bow", "Frozen", "Music", "Hung Up", and "4 Minutes".

Madonna has starred in films such as Desperately Seeking Susan (1985), Dick Tracy (1990), A League of Their Own (1992), and Evita (1996). Although many of her films were not well-received, she won the Golden Globe Award for Best Actress for portraying the titular politician in the lattermost. Her business endeavors encompass the entertainment company Maverick (1992–2009), which included Maverick Records—one of the most successful artist-run labels. Madonna has also pursued fashion brands, written works, health clubs, and filmmaking. She contributes to various charities, having founded the Ray of Light Foundation in 1998 and Raising Malawi in 2006, and advocates for gender equality and LGBT rights.

Madonna is the best-selling female music artist of all time and the first female performer to accumulate US$1 billion from her concerts. She is the only solo act to have at least ten US and UK number-one albums and singles, and holds the record for the most chart-toppers on a singular Billboard chart. Her accolades include seven Grammy Awards, two Golden Globe Awards, twenty MTV Video Music Awards, and an induction into the Rock and Roll Hall of Fame in her first year of eligibility. Madonna was the world's highest-paid female musician for a record eleven years across four decades (1980s–2010s). She has become the subject of various scholarly, literary, and artistic works, giving rise to an academic subfield known as Madonna studies.

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