Rise to Success: Career Highlights of Coolio

How Coolio built a successful career. Explore key moments that defined the journey.

Artis Leon Ivey Jr., known as Coolio, was a prominent American rapper celebrated for his hit single "Gangsta's Paradise" (1995), which earned him a Grammy Award. His music helped broaden hip hop's appeal to a larger audience. Other notable singles include "Fantastic Voyage," "1, 2, 3, 4," and "C U When U Get There." He released nine albums, with his first three, *It Takes a Thief*, *Gangsta's Paradise*, and *My Soul* achieving mainstream success. Coolio initially gained recognition as part of the gangsta rap group WC and the Maad Circle and sold 4.8 million albums in the U.S.

Sections (2)

Full Timeline Career & Achievements

1987: First Single Release

In 1987, Coolio recorded his first single, titled "Whatcha Gonna Do?", marking the beginning of his professional music career.

1988: Collaboration with Nu-Skool

In 1988, Coolio collaborated with Nu-Skool to record "What Makes You Dance (Force Groove)", expanding his presence in the L.A. rap scene.

1991: Joins WC and the Maad Circle

In 1991, Coolio joined the rap group WC and the Maad Circle, becoming a co-contributor to their debut album.

1994: Fantastic Voyage Release

In 1994, Coolio released "Fantastic Voyage," one of his most successful singles. Also in 1994, he released his debut album, It Takes a Thief.

1994: Signs with Tommy Boy Records and Releases 'It Takes a Thief'

In 1994, Coolio signed a recording contract with Tommy Boy Records and released his debut solo album, 'It Takes a Thief'.

1995: "Gangsta's Paradise" Release and Success

In 1995, Coolio released "Gangsta's Paradise" for the film Dangerous Minds, which became a global hit and topped the Billboard Hot 100 for three weeks.

1995: Gangsta's Paradise Success

In 1995, Coolio released "Gangsta's Paradise", which became a Grammy Award-winning hit, helping bring hip hop to a wider audience. Also in 1995, he released the album Gangsta's Paradise which was certified two-times Platinum.

1996: Awareness CD and Kenan & Kel Theme Song

In 1996, Coolio appeared on the Red Hot Organization's compilation CD and recorded "Aw, Here It Goes!" for Kenan & Kel.

1996: Top 40 Hit with "It's All the Way Live (Now)"

In 1996, Coolio had another top 40 hit with the song "It's All the Way Live (Now)" from the soundtrack to the movie Eddie, also featured on "Hit 'em High" from Space Jam.

1996: Guest Appearance on Sabrina, the Teenage Witch

In 1996, Coolio made a guest appearance as himself on Sabrina, the Teenage Witch, showcasing his presence in popular culture.

1996: 1, 2, 3, 4 (Sumpin' New) Release

In 1996, Coolio released the single "1, 2, 3, 4 (Sumpin' New)", which was one of his well known hits.

1997: My Soul Album Release

In 1997, Coolio released his third solo album, My Soul, which contained the hit "C U When U Get There" but did not reach the same level of success as his previous albums.

1997: C U When U Get There Release

In 1997, Coolio released the single "C U When U Get There", which was part of his success in the music industry.

1998: Appearance on The Nanny

In 1998, Coolio appeared in an episode of The Nanny, portraying a nerdy character transformed into a rapper, displaying his versatility.

2001: Coolio.com Album Release

In 2001, Coolio released the album Coolio.com, which did not chart on any Billboard chart.

2001: First Appearance as Kwanzaa-bot

In 2001, Coolio voiced Kwanzaa-bot in Futurama, beginning his role in spreading awareness about Kwanzaa through animation.

2002: Appearance on Charmed

Coolio appeared in a 2002 episode of Charmed, playing the role of a Lazarus Demon, adding to his acting roles.

2003: El Cool Magnifico Album Release

In 2003, Coolio released the album El Cool Magnifico, which did not chart on any Billboard chart.

2004: Appearance on Comeback

In 2004, Coolio appeared as a contestant on Comeback – Die große Chance, a German talent show, seeking a career resurgence.

2006: The Return of the Gangsta Album Release

In 2006, Coolio released the album The Return of the Gangsta, which did not chart on any Billboard chart.

July 2008: Spokesperson for Environmental Justice

In July 2008, Coolio became a spokesperson for Environmental Justice and Climate Change, educating students about climate change.

2008: Coolio's Rules Premiere

In 2008, Coolio created and released the reality television show Coolio's Rules, marking his entry into television production.

2008: Cookin' with Coolio Launch

In 2008, Coolio hosted the online cooking show Cookin' with Coolio, showcasing his culinary talents.

2008: Steal Hear Album Release

In 2008, Coolio released the album Steal Hear, which did not chart on any Billboard chart.

2009: Celebrity Big Brother 6

In 2009, Coolio appeared as a housemate on Celebrity Big Brother 6, where he placed 3rd, showcasing his personality on reality TV.

2009: From the Bottom 2 the Top Album Release

In 2009, Coolio released the album From the Bottom 2 the Top, which did not chart on any Billboard chart.

2010: Ultimate Big Brother

In 2010, Coolio appeared on the UK's Ultimate Big Brother, voluntarily leaving after confrontations, highlighting challenges in reality TV.

January 2012: Celebrity Cook-Off Participation

In January 2012, Coolio participated in Rachael vs. Guy: Celebrity Cook-Off, representing the Music Saves Lives Organization, showing his culinary skills and charitable involvement.

June 30, 2013: Tipping Point: Lucky Stars Appearance

On June 30, 2013, Coolio appeared on the UK game show Tipping Point: Lucky Stars, where he came in second, showcasing his participation in UK television.

October 2014: "Fuck the DJ" Premiere

In October 2014, Coolio was featured on the international collaboration track "Fuck the DJ" by UK rapper Blacklisted MC, along with other artists.

2014: Guest Star on Black Jesus

In 2014, Coolio guest starred on an episode of the Adult Swim show Black Jesus, further expanding his acting portfolio.

July 2016: Performs on Greatest Hits

In July 2016, Coolio performed on ABC's Greatest Hits, celebrating his musical legacy.

2017: Long Live the Thief Album Release

In 2017, Coolio released the album Long Live the Thief, which did not chart on any Billboard chart.

2019: Featured on Versatile's Track

In 2019, Coolio appeared on the Irish rap group Versatile's track "Escape Wagon", collaborating with international artists.

2020: The Evolution of Hip-Hop Show Creation

In 2020, just before the onset of the COVID-19 pandemic, Ivey started working on 'The Evolution of Hip-Hop', a big-budget Las Vegas show.

2021: Featured on Versatile's Album

In 2021, Coolio was featured on Versatile's album, Fuck Versatile, on the track "Coolio Interlude", continuing his collaborations.

2022: 'The Evolution of Hip-Hop' Project Completed

In 2022, Moseley and Ivey completed 'The Evolution of Hip-Hop' project. The script, choreography, compositions, outline, and behind the scenes video are to be sent to the Moon in 2026 by Quantum Aerospace and SpaceX, aboard the new SpaceX Starship, as a tribute to Ivey.

2023: Final Futurama Appearance

In 2023, Coolio's final appearance as Kwanzaa-bot in Futurama aired, with the episode dedicated to him.

2026: 'The Evolution of Hip-Hop' Project sent to the Moon

In 2026, the script, choreography, compositions, outline, and behind the scenes video from 'The Evolution of Hip-Hop' project are to be sent to the Moon by Quantum Aerospace and SpaceX, aboard the new SpaceX Starship, as a tribute to Ivey.