Black Celebs Who Have Been Engaged More Than Once

Onika Tanya Maraj-Petty (born December 8, 1982), known professionally as Nicki Minaj (), is a Trinidadian-born rapper, singer, and songwriter based in the United States. She is known for her musical versatility, animated flow in her rapping, alter egos and accents. An influential figure in popular music, she first gained recognition after releasing three mixtapes between 2007 and 2009.

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.

Karrine Steffans (born August 24, 1978) is an American author, most notably of the Vixen series of books. She has worked as an actress and as a video vixen, having appeared in more than 20 music videos. In 2007 and 2008, Steffans visited a number of college campuses to speak about her involvement in the hip hop industry and its expectations of women.

Usher Raymond IV (born October 14, 1978) is an American singer, songwriter, dancer, and actor. He is recognized as an influential figure in contemporary R&B and pop music. In 1994, Usher first released his self-titled debut album at the age of 15 and rose to fame in the late 1990s following the release of his second album, My Way (1997). It spawned his first Billboard Hot 100 number-one single "Nice & Slow", and the top-two singles: the title track and "You Make Me Wanna...". His third album, 8701 (2001), saw continued success and contained two number-one singles, "U Remind Me" and "U Got It Bad", as well as the top-three single, "U Don't Have to Call". It sold eight million copies worldwide and won his first two Grammy Awards for Best Male R&B Vocal Performance consecutively in 2002 and 2003.

Michael Joseph Jackson (August 29, 1958 – June 25, 2009) was an American singer, songwriter, dancer, and philanthropist. Known as the "King of Pop", he is regarded as one of the most significant cultural figures of the 20th century. During his four-decade career, his contributions to music, dance, and fashion, along with his publicized personal life, made him a global figure in popular culture. Jackson influenced artists across many music genres. Through stage and video performances, he popularized complicated street dance moves such as the moonwalk, which he named, as well as the robot.

Ye ( YAY; born Kanye Omari West; June 8, 1977), commonly known as Kanye West ( KAHN-yay), is an American rapper, record producer, entrepreneur, and fashion designer. He is widely regarded as one of the greatest and most influential hip hop musicians of all time, as well as one of the greatest musicians of his generation. Born in Atlanta and raised in Chicago, West gained recognition as a producer for Roc-A-Fella Records in the early 2000s, producing singles for several artists and developing the "chipmunk soul" sampling style. Intent on pursuing a solo career as a rapper, he released his debut studio album, The College Dropout (2004), to critical and commercial success. West subsequently founded his record label GOOD Music later that same year.

Alicia Augello Cook (born January 25, 1980) known professionally as Alicia Keys, is an American singer-songwriter. A classically trained pianist, Keys started composing songs when she was 12 and was signed at 15 years old by Columbia Records. After disputes with the label, she signed with Arista Records and later released her debut album, Songs in A Minor, with J Records in 2001. The album was critically and commercially successful, selling over 12 million copies worldwide. It spawned the Billboard Hot 100 number-one single "Fallin'", and earned Keys five Grammy Awards in 2002. Her second album, The Diary of Alicia Keys (2003), was also a critical and commercial success, selling eight million copies worldwide, and producing the singles "You Don't Know My Name", "If I Ain't Got You", and "Diary". The album garnered her an additional four Grammy Awards.

Willard Carroll Smith Jr. (born September 25, 1968) is an American actor, rapper, and film producer. Smith has been nominated for five Golden Globe Awards and two Academy Awards, and has won four Grammy Awards.

Tyrese Darnell Gibson (born December 30, 1978) is an American singer, songwriter, author, rapper, actor, model, VJ, and screenwriter. After releasing several albums, he transitioned into films, with lead roles in several major Hollywood releases. He played Joseph "Jody" Summers in Baby Boy, Angel Mercer in Four Brothers, Roman Pearce in the Fast & Furious films, and Robert Epps in the Transformers film series. According to Billboard, Tyrese has sold 3.69 million albums in the U.S.

Prince Rogers Nelson (June 7, 1958 – April 21, 2016) was an American singer, songwriter, musician, record producer, dancer, actor, and filmmaker. A guitar virtuoso known for his genre-crossing work, wide-ranging singing voice and flamboyant stage appearances, Prince is regarded as one of the greatest musicians of all time. His innovative music integrated a wide variety of styles, including funk, rock, R&B, new wave, soul, psychedelia, and pop. Prince pioneered the late 1970s Minneapolis sound, a funk rock subgenre drawing from synth-pop and new wave.