Queen Latifah (born Dana Elaine Owens) has covered an iconic amount of creative and entrepreneurial ground, spending majority of the last three decades in the spotlight. Long hailed as one of hip-hop’s pioneer feminists, she began singing, beat boxing and rapping while attending Catholic school in New Jersey, even going on to form her first hip-hop group, Ladies Fresh. With the blessing of her mother, she connected with Mark James, a local DJ known as The 45 King, who, along with Latifah, created the Flavor Unit. After The 45 King recorded Latifah’s first solo demo, the record was given to Fab 5 Freddy, the host of Yo! MTV Raps—leading the aspiring emcee to ink her first record deal with Tommy Boy Records.

After Latifah’s first single, “Wrath of My Madness,” was well received in 1988, she toured Europe and performed at Harlem’s Apollo Theater. At age 19, her debut studio album All Hail The Queen (1989) was released, selling more than one million copies, fueled by the legendary anthem “Ladies First” with Monie Love. Latifah released her final album on Tommy Boy Nature of a Sista in 1991. She became CEO of her first company Flavor Unit Records and Management, as well as first tried her hand at acting, scoring her debut role in Spike Lee’s Jungle Fever. Latifah’s third studio album, Black Reign, was released via Motown Records in 1993, with the single “U.N.I.T.Y.” earning her a Grammy Award. At this time, her company had signed 17 rap groups, including Naughty by Nature—all while she landed a starring role on Living Single, appearing on the sitcom from 1993 to 1998. After releasing her fourth album Order in the Court (1998), Latifah shifted her focus on acting and singing. She released two all-singing jazz standard albums, The Dana Owens Album (2004) and Trav’lin’ Light (2007) before returning to hip-hop with 2009’s Persona. Of her many accolades, Queen Latifah became the first female hip-hop recording artist to be nominated for an Oscar. While her solo music career currently remains in hiatus, her acting career often incorporates her talents as a vocalist, such as her critically acclaimed role in Chicago and equally acclaimed portrayal of blues singer Bessie Smith in the 2015 HBO film, Bessie.

Quasimoto (also known as Lord Quas) is the alter ego of Madlib, first manifesting on the illustrious producer’s personal beat tapes at the beginning of his career in the mid-’90s. Although reluctant at first, Madlib decided to further develop his experimental side project by debuting the Quasimoto voice on Peanut Butter Wolf‘s 1999 album My Vinyl Weighs a Ton with fans later piecing it together that Madlib and Quasimoto were one in the same. The conception of Quasimoto stemmed from Madlib hating the sound of his own voice, using the Alias as an artistic way to display his rapping talents. Madlib created Quasimoto’s signature sound by way of rapping slowly and speeding up the recording, in turn developing a distinctive high-pitched voice reminiscent of someone who playfully inhaled helium from a balloon. Initially designed to remain mysteriously unseen, Quasimoto took on an illustrated form, designed by Madlib and Stones Throw art director Jeff Jank. With the mischievous, cigarette-donning character as distinguishing as its eccentric voice, Quasimoto’s full-lengths have been met with critical acclaim with his 2000 debut The Unseen being regarded as one of the most imaginative indie records of the early aughts and landing on several “best of” lists throughout the years. As exemplified throughout his three studio albums, Quasimoto finds out of left field success with stream of conscious-style rapping built on top of a foundation of found samples and jazz-laden, free-spirited production. While Madlib has not brought Quasimoto to life since 2013’s Yessir Whatever, hip-hop fans never know when he’ll turn up again to stir up some trouble.