In 1990, Cobra began working with producer Donovan German and songwriter Dave Kelly on the Penthouse Records label. This partnership spawned a series of major hits in Jamaica, including "Yush", "Gundelero", and "Feeling Lonely" (with Beres Hammond). He released his first full-length in 1991, entitled Bad Boy Talk, and over the next year worked with several different producers on yet more hit tracks ("O.P.P" with King Jammy, "Tek Him" with Bobby Digital, "Be Patient" with Sly & Robbie). In 1991 and 1992, Mad Cobra broke into the UK charts with five number one hits, bringing with it a backlash over some Britons' concerns about the anti-gay sentiments of tracks such as "Crucifixion".
In the wake of his British success, Mad Cobra landed a deal in America with Columbia Records. His next LP was entitled Hard to Wet, Easy to Dry, and featured "Flex", a single which interpolated elements of The Temptations' "Just My Imagination". It was a smash hit, topping the US Rap Singles chart, hitting #7 on the R&B chart, and peaking at #13 on the Billboard Hot 100. The success of the single propelled the album to #125 on the Billboard Top 200, but the follow-up, "Legacy", failed to chart, and for the next several years Cobra's hitmaking remained primarily in Jamaica with songs such as 1993's "Mek Noise" and "Matti Haffie Move". Around this time, Cobra became involved in rivalries with fellow reggae artists Ninjaman and Buju Banton.
In 1994, Cobra returned with Venom, again recording with King Jammy. Jamaican hit singles from the 1994-1995 period included "Length and Bend", "Fat and Buff", and "Selassie I Rules". In 1996, Cobra inked a deal with Columbia Records and released Milkman in the US market. The album peaked at #12 on Billboard's Top Reggae Albums chart and featured a minor hit, "Big Long John", which charted briefly on the US Dance and R&B Singles charts. In 1998, a track with Mr. Vegas entitled "Guns High" charted in some countries in Europe, and a number of re-releases of his Jamaican material were issued on VP. Further albums were issued in 2001 (Cobra) and 2004 (Words of Warning). Most recently, Cobra was heard on "Cobrastyle", a single from Teddybears' 2006 album, Soft Machine.