R&B has a close relationship with hip-hop. Countless crooners have won over the hearts of rap fans throughout the years. While names like Bobby Brown, Bell Biv DeVoe, Mary J. Blige and R. Kelly have successfully attained legendary status as icons in hip-hop culture as well as R&B, Chris Brown is the latest artist in this lineage and may even be able to surpass a few of the names on this list. Born in Tappahannock, Va., Breezy took to performing at an early age, mimicking dance moves from legends like Michael Jackson and Usher and wowing local crowds in his hometown.

The young singer linked up with Hit Mission Records, a local production team impressed by his talent, which lead to Brown recording a demo that landed in the hands of Tina Davis, then-senior A&R executive of Def Jam Records. She would become his manager and help him land a deal with Jive Records. Releasing his self-titled debut, in 2005, Brown instantly became one of the hottest new artists in all of music off the strength of the album's lead single, "Run It!" The track topped the Billboard Hot 100, earning him the title of the first male solo artist to achieve that feat since Diddy in 1997. Chris Brown would debut at No. 2 on the Billboard 200 and move more than three million units worldwide.

That success would prove to be more of an omen of Brown's impending takeover, as his 2007 sophomore LP, Exclusive, would move over two million copies domestically and yield yet another Hot 100 chart-topper in the T-Pain collaboration, "Kiss Kiss." The young crooner has rightfully earned the spot as the next prolific hitmaker in R&B. Since then, he's dropped Graffiti (2009), F.A.M.E. (2011), Fortune (2012), X (2014), Fan of a Fan: The Album (2015) and Royalty (2015). Eight albums in 10 years; this guy lives by the mantra "never not working."

While controversy has been aplenty for Brown over the years, his artistry has failed to take a hit and has even expanded to include him outshining some of the better rappers in the game. Brown's added his own verses to tracks in addition to singing. He's arguably the one that holds the crown as the king of R&B at the moment. Check out our picks for the 20 best Chris Brown songs to date and find out if your favorite made it on the list.

  • "Run It!"

    Chris Brown Featuring Juelz Santana
  • "Gimme That (Remix)"

    Chris Brown Featuring Lil Wayne
  • "Yo (Excuse Me Miss)"

    Chris Brown
  • "Kiss Kiss"

    Chris Brown Featuring T-Pain
  • "With You"

    Chris Brown
  • "Fine China"

    Chris Brown
  • "Take You Down"

    Chris Brown
  • "She Ain't You"

    Chris Brown
  • "Little More (Royalty)"

    Chris Brown
  • "Deuces"

    Chris Brown Featuring Tyga & Kevin McCall
  • "I Can Transform Ya"

    Chris Brown Featuring Lil Wayne & Swizz Beatz
  • "Wall to Wall"

    Chris Brown
  • "No Bullshit"

    Chris Brown
  • "Strip"

    Chris Brown Featuring Kevin McCall
  • "Ayo"

    Chris Brown & Tyga
  • "Loyal"

    Chris Brown Featuring Tyga & Lil Wayne
  • "Poppin"

    Chris Brown
  • "Say Goodbye"

    Chris Brown
  • "Don't Wake Me Up"

    Chris Brown
  • "Look At Me Now"

    Chris Brown Featuring Lil Wayne and Busta Rhymes

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