The views expressed in this article are those of the author and do not necessarily reflect the official policy or position of any other agency, organization, employer or company.

While claiming an undeniable stake in R&B, Chris Brown has carefully emerged as an occasional carrier of bars, resorting to the title of emcee from time to time. Transitioning from one genre into another could be deemed cringeworthy for the wrong artist. But, Brown has mastered a seamless formation and strategy in keeping his rapping at a minimum, leaving the catalog peppered with instances that are few and far between.

Pairing this with quality delivery every time has raised the question of whether or not the crooner would ever consider taking the gig full-time… even if just for a moment.

“For me, I think I would have to progress more as an emcee first,” he previously admitted. “It’s just me having fun and showcasing who I am. So an album, I would have to be taken a hundred percent serious as a rapper… I love it. Music is my passion. Even on my album now, there’s a couple of songs that I rap on. But, as far as a whole album, I don’t know if the world is ready for Chris Brown the rapper.”

Nevertheless, we’ve taken a look at Chris Brown’s most promising entries on the rapping front and have detailed them. Check them out below.

1. “Look At Me Now”

“Lil’ ni—a, bigger than gorilla / ‘Cause I’m killin’ every ni—a that can try to be on my shit.”

When the track arrived in 2011, “Look At Me Now” was the first noted time that Brown switched hats on the mic. He was assisted with the talents of Lil Wayne and Busta Rhymes, surely having significant expectations to live up to. So, when he decided to strip the track of his usual vocals, Breezy made room for a sing-song cadence and a full-blown sixteen. This was the first time he properly positioned himself for the arrival of new entries like it.

2. On Funk Flex’s radio show

“Got the Colombianas in the kitchen / Workin’ with the soda, I ain’t talkin’ ‘bout Coca-Cola / And all this money to the ceilin’, I ain’t worried ‘bout the world / ’Cause I got it sittin’ on my shoulder.”

A visit to Funk Flex’s stomping grounds to drop a few bars is the proper rite of passage for any seasoned rapper. So, when Brown stopped by the Hot 97 station, he proved that he could hang with the best of them. This time around, Flex provided the instrumental to Brown’s “Only” and the artist accomplished the task of flipping more than a few punchlines for a memorable freestyle.

3. “Till I Die”

“Yeah, this Virginia , straight from the country, right there with my kinfolk / Golds in my mouth and they put 26’s on Benzo’s”

The song is pulled from the tracklist of 2012’s Fortune. Once again, Brown set a precedent when he tapped on the shoulders of Wiz Khalifa and Big Sean for a little help on “Till I Die.” On the track, all signs of his vocals are found in muted harmonies that accentuate the its hook. For the most part, he sticks to the title of emcee this time around, and once more, knocks down another mark on his rap sheet.

4. “No Romeo No Juliet”

“50 in this bitch and I ain’t askin’ him for nothin’ / That’s my OG, if a ni—a trippin’, get to bustin’”

On “No Romeo No Juliet,” the Virginia native plays the role of the featured artist as he spars with 50 Cent over the Arthur McArthur-curated backdrop. On it, he notably opens with a Beanie Man reference, employing a patois-influenced delivery before transitioning into his full verse. The track arrived just at the tip of the rollout for Heartbreak On a Full Moon and gave fans a hidden gem in Brown’s repertoire before aptly going in to full-on crooner mode for his forthcoming album.

5. “Remember Me”

“All this Hennessy, this liquor, ‘bout to penetrate / While I’m pushing Lamborghini’s on the interstate.”

Plucked from his Fan of A Fan collaborative album with Tyga, “Remember Me” is another well-crafted creation that finds the singer floating between bars and blissful vocals. Brown successfully situates himself as a veteran in both lanes in this track. The vested star flips the beginning of the track that surfaced initially in 2014 through a studio snippet. He would soon head over to the Los Angeles radio station POWER 106 for another freestyle session, rapping the verse over ScHoolboy Q’s “Studio” instrumental.