Now, he's gearing up for the release of "Worth It All," an album filled with pop, dance and R&B tracks, which is due this fall. It's an album that's been a long time coming.
"'I'm All Yours' has been ready for a year and a half," Jay Sean told CBSNews.com about the lead single on his fourth studio release and his second on Cash Money Records. "I had legal drama last year, which was really difficult and frustrating ... That's all cleared now."
Which is why the album title means a lot to Jay Sean.
"It's called 'Worth it All' for obvious reasons -- because I've been through so much to get it out there," the British-born artist said. "It's a really tough thing I think in an industry and climate where literally people want everything now, and their attention spans are minimal. It used to be OK to have two or three songs out a year -- and those are your singles. Now, they don't want that. They're like, 'OK, I heard that. Next!'"
Although he wouldn't divulge all of the album's collaborators, two singles have already surfaced: one featuring Pit Bull and another with Young Money rapper Tyga. "I've been very blessed to work with some of the biggest in the game," Jay Sean said. Among them? Sean Paul, Lil Jon and Nicki Minaj.
As for writing and recording the new music, it was a collaborative process that found the former medical school student coming up with lyrics and beats before teaming up with other songwriters and producers.
"There are people that I vibe really well with ... It's just about really feeling the song," the singer-songwriter said. "It's such a weird process, songwriting, because you just have to feel it. There's no right or wrong melody or lyric. So when I wrote 'Down' -- when I sang the melody, I sung the word 'Down' for no reason. I don't know why. That's how I came up with the medley. I was like, 'I don't know why I said down, but we got to write a song around it.'"
Jay Sean wants to capture that magic once again with "Worth it All." There's no album release date yet, but fans can expect plenty more appearances and a tour once it arrives. Something Jay Sean hopes will be worth the wait.