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From 1999 to 2004, Wayne chased infatuation with singer and producer Alicia Keys. In the fall of 2005, he met singer and rapper Eve and became engaged to her in March 2006; however, they ended their engagement less than three months later.[180] Carter began dating singer/actress Iggy Azalea in 2009, but they separated in October 2009.[181] In January 2011, Carter dated 18-year-old beauty pageant winner Amber Rose, but they broke up in March 2011.[182] Carter also dated model Amber Rose from August 2010 to January 2011.[183]
For the years 2012–2014, Wayne was in a relationship with Andrea Cornwell[184] for a few months. In 2012, they were arrested and charged with grand larceny for stealing over $18,000 worth of jewelry and $15,000 worth of vintage watches.[185] In May 2013, the court dropped the grand larceny charges in exchange for Carter completing a drug addiction and supervision program.In January 2014, Carter began a relationship with Ciara after months of rumors. In October 2016, the couple announced they were expecting their first child together.[186] On January 25, 2017, their son was born via emergency C-section. CiCi gave birth to her second child with Wayne in December 2018.[187]
In the late 1990s, Wayne began gaining success in New Orleans, where hip-hop was becoming popular. He was noticed by Birdman, the owner and head of Cash Money Records, who eventually signed Wayne to the label. Carter recorded his first mixtape, Tha Block Is Hot, which featured then-unknown artists such as The Notorious B.I.G., Fat Joe, Turk, and Lil' Cease. Tha Block Is Hot was released in early 1998 and eventually reached number 16 on the Billboard Top R&B/Hip-Hop Albums chart. His debut album, debut, was released in 1998. The album, which featured the hit single "A Milli", sold over 500,000 copies[23] and earned a Grammy Award nomination for Best Rap Album.[24] d2c66b5586