Male Celebrity Rappers Who dated Singers

Dwayne Michael Carter Jr. (born September27, 1982), known professionally as Lil Wayne, is an American rapper, singer, and songwriter. He is regarded as one of the most influential hip hop artists of his generation, and is often mentioned among the greatest rappers of all time. Wayne's career began in 1995, when he was signed by rapper Birdman to his record label Cash Money Records, becoming the youngest member of the label at age eleven. From then on, he was the flagship artist of Cash Money Records before ending his association with the imprint in June 2018.

Aubrey Drake Graham (born October 24, 1986) is a Canadian rapper, singer, songwriter, producer, actor, and businessman. Drake initially gained recognition as an actor on the teen drama television series Degrassi: The Next Generation in the 2000s; intent on pursuing a career in music, he left the series in 2007 after releasing his debut mixtape Room for Improvement. He released two further independent projects, Comeback Season and So Far Gone, before signing to Young Money Entertainment in June 2009.

Cornell Iral Haynes Jr. (born November 2, 1974), better known by his stage name Nelly, is an American rapper, singer, and actor. He grew up in St. Louis, Missouri, and embarked on his musical career in 1993 as a member of the Midwest hip hop group St. Lunatics. He signed with Universal Records as a solo act in 1999 to release his debut studio album, Country Grammar (2000). Its two lead singles, "Country Grammar (Hot Shit)" and "Ride wit Me", (featuring City Spud), both entered the top ten of the Billboard Hot 100. The album peaked atop the Billboard 200 and received diamond certification by the Recording Industry Association of America (RIAA). His second album, Nellyville (2002), spawned two consecutive Billboard Hot 100 number-one singles: "Hot in Herre" and "Dilemma" (featuring Kelly Rowland), along with the top-five single, "Air Force Ones" (featuring Murphy Lee and St. Lunatics).

Curtis James Jackson III (born July 6, 1975), known professionally as 50 Cent, is an American rapper, songwriter, television producer, actor, and businessman. Known for his impact in the hip hop industry, he has been described as a "master of the nuanced art of lyrical brevity".

Tupac Amaru Shakur (TOO-pahk shə-KOOR; born Lesane Parish Crooks; June 16, 1971 – September 13, 1996), also known by his stage names 2Pac and Makaveli, was an American rapper and songwriter. Considered to be one of the most influential and successful rappers of all time, academics regard him as one of the most influential music artists of the 20th century and also a politically conscious activist voice for Black America. Shakur is among the best-selling music artists, having sold more than 75 million records worldwide. His lyrical content has been noted for addressing social injustice, political issues, and the marginalization of other African-Americans, but he was also synonymous with gangsta rap and violent lyrics.

Shawn Corey Carter (born December 4, 1969), better known by his stage name Jay-Z (stylized as JAY-Z), is an American rapper, songwriter, record executive, entrepreneur, businessman, and record producer.

Cameron Jibril Thomaz (born September 8, 1987), better known by his stage name Wiz Khalifa, is an American rapper, singer, and songwriter. He released his debut album, Show and Prove in 2006, and signed to Warner Bros. Records in 2007. His Eurodance-influenced single, "Say Yeah", received urban radio airplay, charting on the Rhythmic Top 40 and Hot Rap Tracks charts in 2008, becoming his first minor hit.

DeAndre Cortez Way (born July 28, 1990), better known as Soulja Boy Tell 'Em or simply Soulja Boy, is an American rapper, record producer, actor, streamer and entrepreneur. In September 2007, his debut single "Crank That (Soulja Boy)" peaked at number 1 on the U.S. Billboard Hot 100. The single was initially self-published to the internet, and later became a number-one hit in the United States for seven non-consecutive weeks starting in September 2007. On August 17, Way was listed at number 18 on the Forbes list of Hip-Hop Cash Kings of 2010 for earning $7 million that year.

Lonnie Rashid Lynn (born March 13, 1972), known by his stage name Common (formerly Common Sense), is an American rapper, actor, and writer. He debuted in 1992, with the album Can I Borrow a Dollar?, and gained critical acclaim with his 1994 album Resurrection. He maintained an underground following into the late 1990s. He achieved mainstream success through his work with the Soulquarians.

Nasir bin Olu Dara Jones (born September 14, 1973), known professionally as Nas (), is an American rapper, songwriter, entrepreneur, and investor. The son of jazz musician Olu Dara, Nas has released eight consecutive platinum and multi-platinum albums and has sold over 30 million records worldwide. He is also an entrepreneur through his own record label; he serves as associate publisher of Mass Appeal magazine and the co-founder of Mass Appeal Records.