How did Shaggy go from the Marines to Grammy-winning stardom?

Shaggy. Jamaican-born U.S. Marine and Gulf War veteran who became a 2-time Grammy-winning reggae star behind ‘Oh Carolina’, ‘Boombastic’, ‘It Wasn’t Me’ and ‘Angel’.

In the military

April 12, 1988 to May 4, 1992. Field artilleryman (cannoneer) with 5th Battalion, 10th Marine Regiment, 2nd Marine Division, Camp Lejeune, North Carolina; trained in artillery at Fort Sill, Oklahoma. Deployed December 1990 to April 1991 for Operations Desert Shield and Desert Storm (Gulf War). Left as a Lance Corporal (he was reduced in rank twice for unauthorized absences). Honorably discharged.

The transition

• Born October 22, 1968 in Kingston, Jamaica; moved to Flatbush, Brooklyn as a teenager and enlisted in the Marines in 1988, by his own account because he kept getting fired from civilian jobs.
• His musical voice was born in uniform: drill instructors called him out to sing cadences, and his deep ‘toasting’ voice came from mimicking them.
• While still stationed at Camp Lejeune he drove to New York City on weekends to record; his underground reggae tracks were already playing on London radio that he could hear in Kuwait during the Gulf War.
• Left the Marines in 1992; within about a year his cover of ‘Oh Carolina’ (1993) went to No. 1 in the UK, launching his career.
• He credits Marine discipline (very early starts, very late finishes) for coping with the music business.

What came next

• ‘Oh Carolina’ (1993) reached No. 1 in the UK.
• ‘Boombastic’ (1995) won the Grammy for Best Reggae Album (1996).
• Album ‘Hot Shot’ (2000) certified 8x platinum by the RIAA and was among the best-selling albums of 2001; singles ‘It Wasn’t Me’ and ‘Angel’ both hit No. 1 on the Billboard Hot 100 and in the UK.
• Second Grammy for Best Reggae Album in 2019 for ‘44/876’, his collaboration with Sting; 8 Grammy nominations in total.
• Founded the Shaggy Make a Difference Foundation / Shaggy and Friends benefit concerts (2016 onward), raising over $1 million for Bustamante Children’s Hospital in Jamaica.
• Returns to perform for troops, including a 2023 show at Fort Sill, where he once trained as an artilleryman.

In Shaggy’s own words

“The job thing wasn’t working out. I kept getting fired, so I checked myself into a job I couldn’t get fired from.” (On why he joined the Marines)

“I thought it would be like summer camp” (On his expectations when he enlisted)

“Some people do twenty years in the military and never see a day of combat, I did four and got sent off to war. It’s just destiny, I guess.” (On being deployed to the Gulf War)

“The Marines [were] a good setup for everything I was about to encounter in life that I didn’t.” (Billboard ‘Growing Up’ video series)

“It was preparing me for what was to be the rest of my life and my career” (On his Marine Corps service)

“It had an impact on me being in the music business because the military was preparing me for everything to do with being successful.” (Interview quoted by DancehallMag, May 2023)

Lessons for your own transition

• Your military habits are a hidden skill set: Shaggy’s voice and his work ethic both came straight from the Marines, so list what service built in you, not just your job title.
• Start building the next career before you take off the uniform: he was recording in New York on weekends while still stationed at Camp Lejeune, so his first hit came about a year after discharge.
• Rank at exit does not cap your future: he left as a Lance Corporal with a mixed record and still became a 2-time Grammy winner, because discipline, not rank, is what transfers.

More veterans who made the leap

See them all, and practical steps for leaving after a long career: How do I transition from the military to civilian work after 30 years?.