Upon release, Round 2 received mixed reviews from music critics, who complimented its production and songwriting and was considered to be an improvement from his previous album.

The second single that was supposed to be released was Fall, but due to label problems it was canceled like "Come Here" on his previous album.

It's not a reinvention, either, but the roster of collaborators is almost completely different, and Holiday all but eliminates the tough guy and stoner talk.

"[5] Mark Edward Nero of About.com said Round 2 is a well-sung, well-written, well-produced album, but the one negative is that it's a little bland and leans too much on love songs.

[4] Nathan Slavik of DJBooth stated that Round 2 finds Holiday shifting away from Lac’s harder-edged image in favor of a smoother sound, resulting in a well-crafted album that shows that while Holiday’s got a ways to go before he reaches elite status, no one will ever be able to call him a one-hit wonder again.