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2015 Hollywood Christmas Parade
Source: Alberto E. Rodriguez / Getty

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