Artists like Trick-Trick

Curtis James Jackson III, known professionally as 50 Cent, is an American rapper, actor, television producer, record executive, and businessman. Born in Queens, a borough of New York City, Jackson began pursuing a musical career in 1996. In 1999–2000, he recorded his debut album, Power of the Dollar, for Columbia Records. During a shooting in May 2000, he was struck by nine bullets, causing its release to be canceled and Jackson to be dropped from the label. His 2002 mixtape Guess Who's Back? was discovered by Detroit rapper Eminem, who signed Jackson to his label Shady Records that year.

Ryan Daniel Montgomery, known professionally as Royce da 5'9", is an American rapper. Best known for his association with fellow Detroit rapper Eminem, the two met in 1997 and formed the hip hop duo Bad Meets Evil the following year. Their 2011 single, "Lighters", peaked at number four on the Billboard Hot 100 and preceded the release of their debut extended play (EP), Hell: The Sequel (2011). The song and EP—which debuted atop the Billboard 200—have both yielded Montgomery's furthest commercial success.

David Darnell Brown, better known by his stage name Young Buck, is an American rapper. He was affiliated with Birdman's Cash Money Records in 1997, formed the hip hop collective UTP with Juvenile and Soulja Slim in 2000, and joined 50 Cent's group, G-Unit by 2003. In 2003, he signed with 50 Cent's G-Unit Records, an imprint of Interscope Records to release his debut studio album Straight Outta Cashville (2004) and its follow-up Buck the World (2007), both of which peaked at number three on the Billboard 200 and were met with critical praise.

Keith Grayson, known professionally as DJ Kay Slay, was an American disc jockey (DJ) from Manhattan, New York. He is referred to by The New York Times as "Hip Hop's One-Man Ministry of Insults". He released four studio albums: The Streetsweeper, Vol. 1 (2003), The Streetsweeper, Vol. 2 (2004), The Champions: North Meets South, and More Than Just a DJ (2010). Known for extensive curation of prominent figures in East Coast hip-hop, his albums were met with success in the regional market; his first two were released by Columbia Records. Grayson died from COVID-19 in 2022.

O'Shea Jackson, known professionally as Ice Cube, is an American rapper, songwriter, actor, and film producer. His efforts on N.W.A's 1989 album Straight Outta Compton contributed to gangsta rap's popularity, and his political rap solo albums AmeriKKKa's Most Wanted (1990), Death Certificate (1991), and The Predator (1992) were all critically and commercially successful. He was inducted into the Rock and Roll Hall of Fame as a member of N.W.A in 2016.

Christopher Brian Bridges, known professionally as Ludacris, is an American rapper and actor. Born in Champaign, Illinois, Ludacris moved to Atlanta, Georgia, where he first began rapping. Starting out with a brief stint as a DJ, he formed the record label Disturbing tha Peace in the late 1990s to release his debut studio album Incognegro (1999). After its single, "What's Your Fantasy", became a top 40 hit on the Billboard Hot 100, the album was re-released by Def Jam Recordings as his major label debut, Back for the First Time (2000). The latter album peaked at number four on the Billboard 200 and spawned his second top 40 single, "Southern Hospitality".

Earl Simmons, known professionally as DMX, was an American rapper, songwriter, and actor. His accolades included an American Music Award, a Billboard Music Award, and six Grammy Award nominations. Regarded as an influential figure in the late 1990s and early 2000s and one of the greats of hip-hop, his music is characterized by his "aggressive" rapping style, with lyrical content varying from hardcore themes to personal themes such as trauma or childhood abuse.

Joseph Anthony Budden II is an American broadcaster and former rapper. He first gained recognition with his 2003 single "Pump It Up", which peaked in the top 40 of the Billboard Hot 100 and preceded the release of his eponymous debut studio album (2003). A critical and commercial success, the album peaked in the top ten of the Billboard 200, although it was his only major label release for Def Jam Recordings. He released seven more independent albums to continued critical praise. While doing so, he performed as a member of the hip-hop supergroup Slaughterhouse, who signed with Eminem's Shady Records in 2012; the group released two studio albums. In 2014, he was made fun of in episode nine, "Tombstone," of Loiter Squad's third season, with his beard divorcing him, played by rapper Earl Sweatshirt.

Benjamin David Goldberg, known professionally as Token, is an American rapper, singer, and record producer from Salem, Massachusetts.

Kirk Jones, better known by his stage name Sticky Fingaz, is an American rapper, record producer and actor best known as a member of platinum selling hardcore rap group Onyx.

Westside Connection was an American hip-hop supergroup formed by Ice Cube, Mack 10, and WC. The group's debut album, Bow Down, reached the number two position on the Billboard 200 in 1996 and was certified platinum that same year.

Shawn Corey Carter, known professionally as Jay-Z, is an American rapper, businessman, and record executive. In 2023, Billboard and Vibe ranked him as the greatest rapper of all time. Rooted in East Coast hip-hop, Jay-Z is known for his complex lyricism that often uses double entendres, wordplay, and braggadocio. His music is built on a rags to riches narrative. According to Forbes, he is the wealthiest music artist in history, worth an estimated US$2.8 billion as of 2026.