Jay-Z cheers on Rihanna at Super Bowl 18 years after he 'locked her in office until 3am' to sign her to record deal

Jay-Z attended Super Bowl LVII where Rihanna performed and announced her second pregnancy. Jay-Z and Rihanna have a long working relationship that began in 2005 when she signed with Def Jam Records while Jay-Z was president. Now 35, Rihanna got her start with Jay-Z as a 17-year-old and has since become an international superstar. 

Rihanna's Super Bowl show came after nearly seven years without new music. She recalled being nervous auditioning for Jay-Z 18 years ago, shaking while waiting and being "locked" in the office until 3 a.

m. At the time, Jay-Z was accused of cheating on Beyoncé with the teenaged Rihanna, though her publicist denied the rumor. Rihanna has said she was "star struck" meeting Jay-Z and had "butterflies," struggling to make eye contact with the hip hop mogul.

During her audition, Rihanna performed her debut single "Pon de Replay" and other songs. Jay-Z was impressed, telling her the only ways out were "out the door after you sign this deal. Or through this window.

.." on the 29th floor. Rihanna signed with Def Jam but left after five years. She then signed with Jay-Z's own label Roc Nation. 

Cheering her on: Jay-Z was pictured attending Super Bowl LVII on Sunday, where his protégée Rihanna put on a spectacular performance during the halftime show and revealed she was pregnant

They go way back: The rap superstar, 53, and the Umbrella hitmaker, 35, have a relationship that spans back to 2005, when she signed to Def Jam while Jay-Z was the president; Pictured 2005

Despite their shaky start, Jay-Z and Rihanna developed a strong partnership and lasting friendship. While rumors once swirled about their connection, Jay-Z has been a key figure in Rihanna's career from her teen years through today.

The article is not finished. Click on the next page to continue.

The article is not finished. Click on the next page to continue.