10 wins & 34 nominations
- 2003 Nominee Teen Choice Award
- Choice Music - Male Artist
- 2003 Nominee Teen Choice Award
- Choice Breakout Music Artist
- 2003 Nominee Teen Choice Award
- Choice Music - R&B/Hip-Hop Artist
- 2004 Nominee International Award
- Favorite Breakthrough Artist
- 2018 Nominee iHeartRadio Music Award
- Dance Song of the Year
For "Rockabye"Shared with: Clean Bandit · Anne-Marie
- 2018 Nominee Billboard Music Award
- Top Dance/Electronic Song
For "Rockabye"Shared with: Clean Bandit · Anne-Marie
- 2012 Nominee MTV Europe Music Award
- Best World Stage Live Performance
- 2003 Nominee MTV Europe Music Award
- Best Male
- 2003 Winner MTV Europe Music Award
- Best New Act
- 2006 Winner American Music Award
- Favorite Pop/Rock Male Artist
- 2003 Nominee American Music Award
- Favorite Rap/Hip-Hop Male Artist
- 2023 Nominee Billboard Latin Music Award
- Crossover Artist of the Year
- 2022 Nominee Premio Lo Nuestro
- Song of the Year - Urban Pop/Dance (Canción Del Año – Pop Urbano/Dance)
For "Mambo"
- 2022 Nominee MOBO Award
- Best Caribbean Music Act
- 2021 Nominee MOBO Award
- Best Reggae Act
- 2013 Winner MOBO Award
- Best Reggae Act
- 2012 Winner MOBO Award
- Best Reggae Act
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