Vanilla Ice

BIOGRAPHy

“Ice Ice Baby” became a number one hit late in 1990, thanks to the pulsating bass riff from David Bowie and Queen’s “Under Pressure.” To the Extreme also went to the top of the charts, spending 16 weeks at number one. Vanilla Ice’s second major album was a live version of To the Extreme. Entitled Extremely Live, it was certified gold. In 1996, Ice made his next appearance (credited as “Rob Van Winkle”), on the track “Boom” by suburban Philadelphia rappers The Bloodhound Gang. The track’s deep bass groove and Ice’s uncharacteristic tough guy flow on the first verse led to a quasi-ironic underground revival in popularity, and the first new Vanilla Ice CD in four years, Hard to Swallow. In August 2005, Van Winkle released his fifth studio album, Platinum Underground. In September 2008, Van Winkle recorded the cover album, Vanilla Ice Is Back! at the label’s request. The album was released in November 2008, and contained covers of songs by Public Enemy, House of Pain, Bob Marley and Cypress Hill. In 2009, Van Winkle started filming a reality television series called The Vanilla Ice Project, which premiered on DIY Network in October 2010. The season is focused on renovating a house in Palm Beach, Florida with each episode dedicated to a different room in the house. Van Winkle, the man once known as Vanilla Ice, continues to tour and draw big crowds.

 

Career Path

1990Released 'To the Extreme,' powered by 'Ice Ice Baby' and its borrowed bass riff from Bowie and Queen's 'Under Pressure'; the album spent 16 consecutive weeks at number one and was certified seven times platinum by the RIAA, making it the best-selling rap album of that year.
1991Released 'Extremely Live,' a gold-certified live album drawn from the 'To the Extreme' tour, and starred in the film 'Cool as Ice.'
1996Appeared on The Bloodhound Gang's track 'Boom,' credited as Rob Van Winkle; the tough-guy verse sparked a quasi-ironic underground revival and led directly to his first new studio album in four years, 'Hard to Swallow.'
2005Released the fifth studio album 'Platinum Underground,' marking his continued presence as an independent artist outside major-label constraints.
2008Recorded and released 'Vanilla Ice Is Back!,' a covers album featuring reimagined tracks from Public Enemy, House of Pain, Bob Marley, and Cypress Hill.
2010Launched 'The Vanilla Ice Project' on the DIY Network, a reality series documenting his renovation of South Florida mansions that ran for nine seasons through 2020.
2016Competed on 'Dancing with the Stars,' extending his pop-culture footprint well beyond hip-hop into mainstream television audiences.
2023Headlined the 'I Love the 90s' tour alongside a rotating lineup of artists including Naughty By Nature, Color Me Badd, and All-4-One, drawing large crowds on a circuit he has anchored since 2016.
2024'To the Extreme' biopic with Dave Franco attached to play Van Winkle moved toward pre-production, with Franco in regular contact with the rapper sourcing stories from different periods of his life.
2025Returned to headline the 'I Love the 90s Tour,' now rebranded as 'Forever Young' in select markets, with dates running from Tucson through the fall festival season.

Book Vanilla Ice | Request A Quote

This site is designed for talent buyers interested in contracting artists for live performance at corporate, private functions and special events. Please be aware that all our contracts require pre-show secured financial commitments (binders and/or deposits).

We also regret that for legal and contractual reason we cannot respond to inquiries related to any of the following:

  • Requests for artist to play at non-paying fundraisers.
  • Requests to fwd. messages or for contact information.
  • Invitations to appear to accept awards, donate items for auctions, etc.
  • Requests for print, radio or TV interviews.
  • Upcoming public appearances of artist on the site.
  • Requests regarding TV or film projects.
  • Requests to forward jokes, songs, lyrics, etc.

In order for us to best understand your needs, we appreciate initial contact to be through the form below. If you prefer to speak with someone or your inquiry requires more immediate attention, please call us at 888.552.6737.

Regular office hours are Monday–Friday, 10:00 AM – 7:00 PM (EST).

We typically respond within 24 hours

WHAT OUR CLIENTS SAY

HOW BOOKING WORKS

We make hiring top entertainment simple with our easy 3-step process.

01
INQUIRE

Tell us about your event,
date, and your vision
for entertainment.

02
WE HANDLE
DETAILS

We work directly with the talent’s team to negotiate
and coordinate.

03
ENJOY YOUR
EVENT

Relax and enjoy as we
ensure a seamless,
memorable experience.

WHY CHOOSE HEADLINE ENTERTAINMENT

20+

Years of industry
experience.

600+

Professional
Entertainers.

5,000+

Successful Events.

500

Trusted by Fortune
Companies.

Celebrity Entertainment Booking Agent - Headline Entertainment

PREMIER BOOKING AGENCY FOR CELEBRITY TALENT

Your trusted source for America’s top corporate comedians, musical acts, and celebrity entertainment. Our philosophy is simple: deliver exceptional acts and expert guidance to make your corporate event, fundraiser, or private celebration unforgettable from start to finish.

Our discerning eye for talent, industry experience, and impeccable service sets us apart. Using long-standing entertainment industry relationships, we secure the right performers for your event at the right price. From affordable local headliners to world-famous celebrities, we ensure your next corporate meeting, gala, fundraiser, or special event becomes the success you need.

Ready to book your perfect entertainment? Contact us today for a personalized quote.