Artists like Freeway

Jason Terrance Phillips, better known by his stage name Jadakiss, is an American rapper who began his career in the 1990s and formed the hip hop trio the Lox alongside Styles P and Sheek Louch in 1994. The group signed with Puff Daddy's Bad Boy Records, an imprint of Arista Records to release their debut studio album, Money, Power & Respect (1998); their second album, We Are the Streets (2000) was released by Ruff Ryders Entertainment, an imprint of Interscope Records. Both peaked within the top five of the Billboard 200 and yielded critical praise; their two subsequent albums, Filthy America... It's Beautiful (2016) and Living Off Xperience (2020) were both released by Jay-Z's Roc Nation and met with continued praise.

LaRon Louis James Sr., better known by his stage name Juelz Santana, is an American rapper. A member of now-defunct hip-hop group the Diplomats, he is best known for his appearances on Cam'ron's 2002 singles "Oh Boy" and "Hey Ma", both of which peaked within the top five of the Billboard Hot 100. He later guest appeared on Chris Brown's 2005 single, "Run It!", which peaked atop the chart for five weeks and received triple platinum certification by the Recording Industry Association of America (RIAA). As a lead artist, he is also known for his 2005 single "There It Go ", which peaked at number six on the chart and received platinum certification by the RIAA.

John David Jackson, known professionally as Fabolous, is an American rapper. Raised in Brooklyn, he first gained recognition for his ability upon performing live on DJ Clue's Hot 97 radio show. Jackson then signed to Clue's record label Desert Storm Records, in a joint venture with Elektra Records. He rose to further prominence with his debut studio album Ghetto Fabolous (2001), which spawned the hit singles "Can't Deny It" and "Young'n ." Adopting a further commercially-oriented approach, his second album, Street Dreams (2003), was supported by the singles "Can't Let You Go" and "Into You" —both of which peaked at number four on the Billboard Hot 100.

Barry Adrian Reese, better known by his stage name Cassidy, is an American rapper. He first garnered attention for his freestyles and competitions as a battle rapper in the late 1990s, and formed the Philadelphia-based hip hop collective Larsiny by the end of the decade. American record producer Swizz Beatz discovered the group in 2000 and signed Cassidy to his newly-established Full Surface Records, in a joint venture with J Records. He adopted a commercially-oriented approach for his 2003 debut single "Hotel" and its follow-up, "Get No Better" ; the former peaked at number four on the Billboard Hot 100 while both preceded the release of his debut studio album, Split Personality (2004).

Moses Michael Levi Barrow, best known by his stage name Shyne, is a Belizean politician and former rapper. He served as Leader of the Opposition in the House of Representatives, and the leader of the Belize United Democratic Party.

The Diplomats were an American hip hop collective formed in the summer of 1997 by childhood friends Cam'ron and Jimmy Jones in Harlem, New York City. The group was originally composed of Cam'ron, Jim Jones and Freekey Zekey, all of whom grew up together in Harlem. In 1999, fellow Harlem-based rapper Juelz Santana joined the group.

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.

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.

Mason Durell Betha, known professionally as Mase, is an American rapper. Best known for his work with Sean "Puff Daddy" Combs' Bad Boy Records, he signed with the label in 1996 and quickly found mainstream recognition as Combs' hype man. He guest appeared on Combs' 1997 single "Can't Nobody Hold Me Down", which peaked atop the Billboard Hot 100, while his first two singles as a lead artist, "Feel So Good" and "What You Want", both peaked within the chart's top ten. Released in October of that year, his debut studio album, Harlem World (1997), peaked atop the Billboard 200 chart, received quadruple platinum certification by the Recording Industry Association of America (RIAA), and spawned his third top ten single as a lead artist, "Lookin' at Me". Furthermore, his guest performances on labelmate the Notorious B.I.G.'s single "Mo Money Mo Problems" and Combs' "Been Around the World" peaked at numbers one and two on the Billboard Hot 100, respectively, that same year.

Ruff Ryders Entertainment is an American hip-hop record label and management company founded by siblings and record executives Joaquin "Waah", Darrin "Dee" and Chivon Dean in 1988. It operated as a subsidiary of Universal, and distributed by Interscope Records, with Def Jam Recordings serving as the distributor for DMX albums. The label went on to launch the careers of several successful artists such as their flagship artist DMX, Eve, The LOX, Drag-On, MC Jin, producers Dame Grease and the Deans' nephew, Swizz Beatz among others. The Ruff Ryders namesake also referred to a loose-knit hip-hop collective composed of the core signees of the label. Ruff Ryders and its main studio Powerhouse Studios are headquartered at 33 South Broadway in Yonkers, New York.

Sean Divine Jacobs, better known by his stage name Sheek Louch, is an American rapper, best known as a founding member of East Coast hip hop trio the Lox, which he formed in 1994 with Jadakiss and Styles P.

Jay Wayne Jenkins, known by his stage name Jeezy, is an American rapper. He is credited, alongside fellow Georgia-based rappers T.I. and Gucci Mane, with pioneering the hip hop subgenre trap music for mainstream audiences. Jenkins began his career in 2001, releasing two independent albums until signing with Def Jam Recordings to release his major label debut, Let's Get It: Thug Motivation 101 (2005). The album peaked at number two on the Billboard 200, sold 172,000 copies in its first week, and received double platinum certification by the Recording Industry Association of America (RIAA); its lead single, "Soul Survivor", peaked at number four on the Billboard Hot 100 and remains his highest-charting song.

Clifford Smith Jr., known professionally as Method Man, is an American rapper, record producer, and actor. He is a member of the East Coast hip-hop group Wu-Tang Clan, and is half of the hip-hop duo Method Man & Redman. His debut solo album, Tical (1994), peaked at number four on the Billboard 200 and spawned the single "I'll Be There for You/You're All I Need to Get By", which won Best Rap Performance by a Duo or Group at the 38th Annual Grammy Awards. The song also peaked within the top five of the Billboard Hot 100; he and Blige later starred in Power Book II: Ghost, a spin-off of Power.

M.O.P. is an American hip-hop duo composed of rappers Billy Danze and Lil' Fame, best known for their song "Ante Up." The group has frequently collaborated with DJ Premier. The group is part of the Gang Starr Foundation. Fame occasionally produces under the moniker Fizzy Womack and has produced tracks on every M.O.P. release since 1996's Firing Squad. He has also worked for other artists, including Kool G Rap and Wu-Tang Clan.

Talib Kweli Greene is an American rapper. He is one half of the hip-hop duo Black Star, which he formed in 1997 with fellow Brooklyn rapper Mos Def. Their 1998 single, "Definition", entered the Billboard Hot 100 and preceded their eponymous debut album (1998), which entered the Billboard 200. The duo then began pursuing solo careers, although one further Black Star album — No Fear of Time (2022) — was released thereafter.

Christopher Lee Rios, better known by his stage name Big Pun, was an American rapper. Emerging from the underground hip-hop scene in the Bronx, he came to prominence upon discovery by fellow Bronx rapper Fat Joe, alongside Cuban Link and Triple Seis, and thereafter guest appeared on his 1995 album Jealous One's Envy.

Robert Ross, known professionally as Black Rob, was an American rapper who was signed to Sean "Puffy" Combs' Bad Boy Entertainment. He was best known for his 2000 single "Whoa!", which peaked at number 43 on the Billboard Hot 100.

EPMD is an American hip hop duo from Brentwood, New York. The duo's name is an initialism for "Erick and Parrish Making Dollars", referring to its members: emcees Erick Sermon and Parrish Smith. During an interview on college radio station WHOV in 1987, Parrish Smith stated that the name evolved from the original: "We were originally known as "EEPMD", but chose to go with EPMD because it was easier to say." He also stated that they dropped the two "E's" because N.W.A's Eric Wright was already using "Eazy-E" as his stage name. The group has been active for 39 years.