#WordOnTheStreet Underrated Legends Vol 6 : Sean Kingston
#WordOnTheStreet Underrated Legends Vol 6 : Sean Kingston

It’s #WordOnTheStreet Sunday and on the final Underrated Legends featuring music artist of 2025, we look at one of the most underrated artist that was running the game for both the Pop charts and the Hip Hop/R&B charts. What is that? Who is that? The in denial…but undeniable Sean Kingston.
Sean Kingston began his career back in 2007, bursting on the scene with the now iconic, but then polarizing but popular record, “Beautiful Girls.” Like Soulja Boy, he got his start on YouTube and while “Crank Dat” came out first and was more widely recognized as the start of a revolution…Sean Kingston rose to fame first and became the first 90’s born artist to top the Billboard Hot 100. He beat Soulja Boy with that accolade by only a very close 6 weeks.
Sean Kingston initially gained a lot of backlash for the usage of the word “suicdal,” but the record ended up instantly becoming one of the biggest records in all of music at the time.
Sean Kingston dominated the airplay charts among multiple genres including mainstream pop and urban rhythmic. In the mid 00’s, Kingston was dropping consistent bangers with his own reggae style of Hip Hop and R&B. His music was one of the key focal points in the iconic, “Now That’s What I Call Music” series and was a staple of IPOD downloads.
Kingston was nominated for a litany of awards throughout his run including recently winning a Grammy Award alongside Chris Brown, as a co-writer for Sensational, a number of Teen Music, Kid Choice, IHeart, and Juno Awards
Kingston made several appearance of shows, most notably on Disney Channel‘s Suite Life on Deck and obviously he was one of those iconic 106 and Park era artist.
Let’s look back at some of his classic records. Let’s start with the bangers that started it all and had 2007-2008 on a different type of lit.
SEAN KINGSTON – BEAUTIFUL GIRLS
SEAN KINGSTON – TAKE YOU THERE
BABY BASH FT SEAN KINGSTON – WHAT IS IT
NATASHA BEDINGFIELD FT SEAN KINGSTON – LOVE LIKE THIS
Kingston didn’t stop applying pressure either.
SEAN KINGSTON – ME LOVE
SEAN KINGSTON – FIRE BURNING
SEAN KINGSTON FT WALE – SENSATIONAL LOVE
SEAN KINGSTON FT JUSTIN BIEBER – EENIE MEENIE
SEAN KINGSTON – DUMB LOVE
MIMS FT SHA DIRTY, RED CAFE, AND SEAN KINGSTON – LIKE THIS REMIX
and who can forget them 2013 summer vamping days, iykyk
SEAN KINGSTON FT CHRIS BROWN, WIZ KHALIFA – BEAT IT