In 2008, he won a Grammy with rapper Kanye West for the single "Good Life". In 2010, he won another Grammy with Jamie Foxx for the single "Blame It".
T-Pain was featured on the hit single "All I Do Is Win" by DJ Khaled, along with the remix. He was also featured on Wisin & Yandel's single "Imaginate" & Bun B's single "Trillionaire." In 2010, he was featured on hit singles like Pitbull's "Hey Baby (Drop It To The Floor)" and Nelly's "Move That Body." He was also featured on another single by Wisin & Yandel along with rapper 50 Cent called "No Dejemos Que Se Apague." The last two single's T-Pain was featured on in 2010 were the official Remixes to Black & Yellow by rapper Wiz Khalifa & Loving You No More.
T-Pain was featured on the first single by DJ Khaled called "Welcome To My Hood" off his new album We the Best Forever. The song featured him along with Rick Ross, Plies, & Lil Wayne. He is also expected to be featured on albums such as Drake's Take Care, Lil Wayne's Tha Carter IV, Tech N9ne's All 6s and 7s, and many more. T-Pain is featured on a single called Electroman which is by house artist Benny Benassi. In January, JRandall released a single, "Can't Sleep", featuring T-Pain and in March 2011 the next single off RevolveR was released titled "Best Love Song" and features Chris Brown.