Before Jay-Z lucked up with his future wife, Beyonce Knowles, he had a crush on another singer, Aaliyah, who was dating Damon Dash at the time.
Dash, who co-founded Roc-a-Fella Records with Jay-Z, says his former business partner "tried very hard" to get with Aaliyah, but she wasn't impressed with him.
Dash, now 48, dated Aaliyah for about a year until she died in a plane crash at age 22 in 2001.
Jay-Z was the odd man out in this photo dated July 2, 2000. (L-R) Natane Adcock, Damon Dash, Aaliyah, Jay-Z, Sean "Puff Daddy" Combs and Jennifer Lopez partied together at Combs' Fourth of July party in the Hamptons.
Although they were not formally engaged, Dash says he and Aaliyah were planning to get married and raise a family.
Dash claims Jay-Z tried his best to woo Aaliyah away from him. He said Jay-Z "went hard" at Aaliyah but she curved him repeatedly. Even though she was dating Dash, Jay-Z couldn't keep his paws off of Aaliyah.
In this photo dated May 6, 2000, Jay-Z is hugged up on Aaliyah at a Tommy Hilfiger party in Los Angeles. Also pictured are Bijou Phillips, 2nd from right, and Quincy Jones' daughter Kidada Jones, who dated rapper LL Cool J from 1992 to 1994.