Current age: 34
Career at 20: Coming off being named model of the year at the VH1/Vogue Fashion Awards in 1999, Gisele began her reign as a Victoria's Secret Angel in 2000. That year she secured a $25 million, record-breaking contract with the lingerie brand, and Rolling Stone put Gisele on its cover, calling her the most beautiful girl in the world.
Relationship at 20: In 2000, Gisele started her five-year relationship with Leonardo DiCaprio.
Quoted at 20: In an interview with Time magazine, Gisele humbly explained her appeal: "I think guys like me because they like girls in lingerie. They like any girl in lingerie."