The actress fell for the producer while shooting an ad for LA Gear. Within a year of dating, they had moved in together, but called it quits in 1994.
When all was said and done, Benji Madden was the one to come away with Cameron Diaz's heart, marrying her in an intimate ceremony on Jan. 5. But for 42 years, the actress remained a bachelorette — and dated a bevy of hunks along the way! We revisit the most memorable ones.