Possible Clues:

• Rapper whose debut studio album was 1990's "To the Extreme"
• Rapper with the album 'To the Extreme'
• *Robert Matthew Van Winkle's rap name
• Chilly 1990s rap star
• Rapper whose name sounds like a dessert
• Singer with the 1990 #1 album 'To the Extreme'
• "To the Extreme" rapper
• 'To the Extreme' rapper
• "Cool" rapper with the 1990 album "To the Extreme"