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- Tonio D Don
- Tony Bailey
- Tony Prescott
- Tony Wylie
- Too Real
- Top Cat
- Top Notch Swift (TNS)
- TopRo
- Tori Elle
- Tosheena
- TR Shine
- Tracy D
- Travis World
- Trendsetter
- Trevor St. John
- Trey Breezy
- Tricia Lee Kelshall
- Trilla-G
- Trini Baby
- Trini Dutch
- Trini Jacobs
- Triniboi Joocie
- Trinidad Killa
- Trinidad Rio
- Trinity Clarke
- Trisha Hamilton
- Truvinchi
- Ttrevvle
- Tuff House
- Turner
- Twiggy
- Twin
- Twixx
- Tynie
- Tyrel
- Ultimate Rejects
- Umi
- Umi Marcano
- Umpa
- Uncle Ellis
- V'ghn
- V’ghn
- Valene Nedd
- Valentino King
- Valiant
- Van Basten
- Vanessa Ramoutar
- Vee Ram
- Veekash
- Verrse
- Vershon
- Viking Ding Dong
- Vinel Hinds
- Vintayge
- Vocalking
- Voice
- Vybz Kartel
- VybzStarr
- W*A*R*D
- Wadicks
- Wally Kyat
- Wassy K
- Wendi
- Wendy Scantlebury
- Wettle Beatz
- Wetty
- Wetty Beatz
- White Wine
- Wickedy
- WildxFire
- x Barii
- XL
- XplicitMevon
- Xposer
- Yakstar
- Yankey Boy
- Yelo
- Young Bredda
- Young Lyrics
- Youni-T
- Yung Bredda
- Yung Image
- Yung Kymani
- Yung Pert
- Yung Seeche
- Zamoni
- Zan
- Zantelly
- Zari
- Zebee
- Zeek
- Zeron
- Zess Prince
- ZigBoi
- Ziggy Rankin
- Zion I
- Zito
- ZJ Sparks
- Zwade
