Vanilla Ice

In late 1990, Ice began an eight-month relationship with Madonna, and appeared in photographs for her book, Sex. In April 1991, Ice began to film the SBK-produced Cool as Ice, in which he played a leading role. Cool as Ice opened on October 18, 1991, in 393 theaters in the United States, grossing $638,000, ranking at #14 among the week's new releases. Reviews of the film were negative and he received a Golden Raspberry Award for Worst New Star.

Although he 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.

Ice attempted suicide with a heroin overdose on July 4, 1994, but was revived by his friends. After being revived, Ice decided that it was time to change his lifestyle. He was inspired to change his musical style and lifestyle. While his later albums haven't charted or featured much radio airplay because of their less mainstream, rock-oriented sound, he has a loyal underground following. His return to music in 1998, Hard to Swallow went gold while his other releases Bi-Polar and Platinum Underground have done well. Uncertain about his future career, Ice studied real estate and started working on the side renovating and selling houses. In late 1995, he set up a recording studio in Miami and joined a grunge band, Pickin Scabz.

In 2009, he began hosting The Vanilla Ice Project, a home renovation show in Florida, on DIY Network. In 2011, Ice published a book on the subject, Vanilla Ice Project – Real Estate Guide, on how to succeed in real estate. In June 2011, he filmed a role in the movie That's My Boy, starring Adam Sandler and Andy Samberg,

His sixth studio album, WTF - Wisdom, Tenacity and Focus, was released on August 19, 2011, through Radium Records. While the record featured an array of different styles, like other recent Vanilla Ice albums, it also featured Ice's return to Electronica.

In 2016, Vanilla Ice competed on season 23 of Dancing with the Stars. He was partnered with professional dancer Witney Carson. On January 4, 2019, Dave Franco was cast to star as Ice in a biopic chronicling the rapper's life.