1999–2006: Early career and Rappa Ternt Sanga T-Pain joined the rap group Nappy Headz in 1999. Through a mutual connection with music promoter TJ Chapman, he was discovered by
Rocco Did It Again! and Mike Blumstein—co-founders of the independent record label Chase Entertainment—to whom he signed. His stage name is short for "Tallahassee Pain", and was chosen because of the hardships he experienced while living there. While T-Pain was offered other record deals, with the highest-bidding being US$900,000, Akon promised the young artist a personal mentorship in the industry. Meanwhile, Blumstein and Rocco remained involved in T-Pain's careers as joint co-
managers. Afterward, T-Pain began singing instead of rapping, and used this inspiration to begin recording for his debut studio album,
Rappa Ternt Sanga. Released on December 6, 2005, through a joint venture with
Jive Records, and number ten on the latter. The third and final single from the album, "Studio Luv", was released in October 2006 and failed to chart.
2007–2008: Epiphany Summer Jam concert In mid-2006, T-Pain began work on his second album, now with the
Zomba Label Group as well as his previous labels. The album, titled
Epiphany, was released on June 5, 2007. The album sold 171,000 records in its first week, reaching number one on the
Billboard 200. The record has since sold 819,000 records in the United States. The album was preceded by the lead single "
Buy U a Drank (Shawty Snappin')" (featuring
Yung Joc), released in February 2007. The song reached number one on both the Hot 100 and Hot R&B/Hip-Hop Songs chart, becoming his first to peak atop both charts. The album's second single, "
Bartender" (featuring Akon), was released in June 2007 and reached number five on the Hot 100 and number nine on the Hot R&B/Hip-Hop Songs chart. The third and final single from the album, "
Church", was released in October 2007 and failed to chart in the United States. Speaking in May 2007 to Pete Lewis of
Blues & Soul about his reason for naming his second album 'Epiphany', T-Pain stated: "One of the two dictionary meanings of epiphany is 'a sudden moment of insight or revelation'. And to me the title 'Epiphany' signifies the moment I realized that, to make the best music I can, I needed to just go in the studio and be myself, and not concentrate so hard on following other people's formulas." While promoting his second album, T-Pain made guest appearances on multiple songs by other artists. T-Pain was featured on "
I'm a Flirt" (remix) by
R. Kelly, "
Outta My System" by
Bow Wow, "
Baby Don't Go" by
Fabolous, "
I'm So Hood" by
DJ Khaled, "
Shawty" by
Plies, "
Kiss Kiss" by
Chris Brown, "
Low" by
Flo Rida, and "
Good Life" by
Kanye West. For two weeks in late 2007, T-Pain was featured on four top ten singles simultaneously on the Hot 100 chart. His performance on West's "Good Life" won the
BET Award for
Best Collaboration and was nominated in several other categories.
2007–2009: Three Ringz In 2007, T-Pain began work on his third album,
Three Ringz with Rocco Valdes, Akon, and
Lil Wayne. The album was also his first under his newly launched label,
Nappy Boy Entertainment. Released on November 11, 2008, the album sold 168,000 records in its first week and reached number four on the
Billboard 200. A mixtape,
Pr33 Ringz, was released in early 2008 for the album's promotion.
Three Ringz was preceded by three singles; its lead single, "
Can't Believe It" (featuring Lil Wayne), was released in July 2008 and reached number seven on the Hot 100 and number two on the Hot R&B/Hip-Hop Songs chart. The album's second single, "
Chopped 'n' Skrewed" (featuring
Ludacris), was released in September 2008; it reached number 27 on the Hot 100 and number three on the Hot R&B/Hip-Hop Songs chart. The third and final single from the album, "
Freeze" (featuring Chris Brown), was released in October 2008; it reached number 38 on the Hot 100 and number 39 on the Hot R&B/Hip-Hop Songs chart. Guest appearances on
Three Ringz include
T.I., Lil Wayne, Ludacris, DJ Khaled,
Ciara, Chris Brown, and Kanye West, among others. In 2008, T-Pain continued to guest perform on numerous singles, such as "
She Got It" by
2 Pistols, "
Go Girl" by Ciara, "
The Boss" by
Rick Ross, "
Cash Flow" by
Ace Hood, "
Shawty Get Loose" by
Lil Mama, "
One More Drink" by Ludacris, and "
Go Hard" by DJ Khaled. T-Pain and Ludacris collaborated to perform "Chopped 'n' Skrewed" and "One More Drink" on American late-night television programs
Jimmy Kimmel Live! on
ABC in November 2008 and on
NBC's
Saturday Night Live in the same month. T-Pain appeared again on
SNL in February 2009 (
season 34, episode 15, hosted by
Bradley Cooper with musical guest
TV on the Radio) as a feature in the
Digital Short premiere of
The Lonely Island's single, "
I'm on a Boat," off their album
Incredibad. T-Pain also supported the album in 2009 with his
Thr33 Ringz Tour, which included sold-out shows across North America. T-Pain and Lil Wayne formed the duo T-Wayne in 2008. The duo released a self-titled mixtape in late 2008; it charted on the
Billboard 200 in January 2009. Their debut album was going to be released in 2009, but never was.
2009–2012: Revolver He collaborated with
Taylor Swift for the
CMT Music Awards, performing "Thug Story", a
parody of Swift's hit single "
Love Story". In an interview with
MTV, T-Pain announced that he would release his fourth studio album in November 2009 and that its title would be
UBER. He stated that although he originally wanted to release the album in the summer of 2010, his label had pushed the release forward. However, the album was not released in 2009. An
iPhone application called "I Am T-Pain", featuring an
auto tuner, allowing fans to record and modify their own voice to accompany an instrumental collection of T-Pain's music, was released in September 2009. In July 2009, T-Pain endorsed the 2009 T-Pain Killa Cam-Pain, a grassroots effort to help him become elected as
president of
Florida State University. In November 2009, T-Pain released the first single from his fourth studio album, "
Take Your Shirt Off". The single only managed to reach number eighty on the Hot 100, and was later dubbed a promotional single. In February 2010, he released "
Reverse Cowgirl" (featuring
Young Jeezy), which was the official lead single from his fourth studio album. He later release an updated version of the song excluding Young Jeezy's verse and adding a new bridge. The single reached number seventy-five on the Hot 100 and number sixty-four on the Hot R&B/Hip-Hop Songs chart, becoming a mild hit. The single has since been dubbed a promotional single. T-Pain was later featured on the "
We Are the World 25 for Haiti" single in February 2010, which reached number two on the Hot 100. In March 2010, T-Pain developed and starred in
Adult Swim's animated musical special,
Freaknik: The Musical. T-Pain released a mixtape on his Nappy Boy label in February 2010,
T-Pain Presents: Nappy Boy All Stars Vol.1, which contained remixes of songs including "
Forever" by
Drake. On May 5, 2011, he announced another mixtape,
Prevolver, serving as a predecessor to his album. The mixtape including collaborations from artists such as Lil Wayne and
Field Mob. In June 2010, T-Pain confirmed that his fourth studio album, now titled
Revolver, had been completed and mastered, but that it would not be released until album sales increase. T-Pain's first feature film,
Lottery Ticket, was released on August 20, 2010. In October 2010, T-Pain release his third promotional single, "
Rap Song". The song charted poorly, peaking at 89 on the Hot 100. T-Pain was featured on the hit single "
All I Do Is Win" by DJ Khaled, along with the remix. He featured on
Wisin & Yandel's single "
Imaginate" and
Bun B's single "
Trillionaire". In the last two quarters of 2010, he was featured on the hit singles "
Hey Baby (Drop It to the Floor)" by
Pitbull, and "
Move That Body" by
Nelly. He was also featured on another single by Wisin & Yandel along with
50 Cent called "
No Dejemos Que se Apague". The last two singles T-Pain was featured on in 2010 were the official remixes to "
Black and Yellow" by
Wiz Khalifa and "
Loving You No More" by
Diddy – Dirty Money. in 2012 T-Pain was featured on the first single by DJ Khaled called "
Welcome to My Hood" off his 2011 album
We the Best Forever. The song featured him along with Rick Ross, Plies, and Lil Wayne. He was also featured on albums such as Drake's
Take Care, Lil Wayne's
Tha Carter IV, and
Tech N9ne's ''
All 6's and 7's''. A new toy called "iAm T-Pain Microphone" was released in 2011, at the price of $39.99. On January 29, 2011, T-Pain was featured on Italian DJ
Benny Benassi's song "Electroman", released as the third single in the
album of the same name. In January, JRandall released a single, "Can't Sleep", featuring T-Pain. On March 22, 2011, the next single from
Revolver, "
Best Love Song" (featuring Chris Brown), was released. On
Twitter, T-Pain stated that he would release his mixtape
Prevolver when he got 500,000 followers and release his album
Revolver when he got 1,000,000 followers. Also in 2011, he appeared on another Adult Swim series: the sixth-season premiere episode of
Squidbillies, performing a version of the theme song in addition to the original song "(I Like) Drivin' In My Truck" with
Unknown Hinson; this song was released in 2012 as part of the free digital album
The Squidbillies Present: Music for Americans Only Made by Americans in China for Americans Only God Bless America, U.S.A. on the Adult Swim Music website. On October 7,
RCA Music Group announced it was disbanding Jive Records along with
Arista and
J Records. With the shutdown, T-Pain (and all other artists previously signed to these three labels) would henceforth release all material (including
Revolver) on the
RCA Records brand. The album
Revolver was eventually released in December 2011, alongside the transatlantic Top 10 single "
5 O'Clock", which features
Lily Allen and Wiz Khalifa.
2013–2017: Oblivion On April 1, 2013, after the announcement of T-Pain cutting off his signature dreads, he announced the title of his fifth studio album, then entitled
Stoicville: The Phoenix stating, "To me, a Phoenix represents new beginnings. A new era, a new life, I'm rising from the ashes." Prior to releasing his fifth studio album, he released
T-Pain Presents Happy Hour, a greatest hits compilation. Its first single, "
Up Down (Do This All Day)" (featuring
B.o.B), produced by
DJ Mustard, was officially released on August 13, 2013. The song peaked at number 62 on the
Billboard Hot 100. The second single "Drankin Patna" was released a year later on July 21, 2014. On November 7, 2014, T-Pain premiered the intro and title track off of
Stoicville. On November 21, 2014, T-Pain premiered "Coming Home" as the first promotional single in support of
Stoicville and made it available for free on his official website. On June 8, 2015, T-Pain released a song titled "Make That Shit Work" (featuring
Juicy J). Following another delay, T-Pain confirmed the album was still on its way, missing its December 11 expected release date to further delay. On December 9, 2015, to mark the one-year anniversary of the most popular Tiny Desk Concert ever and the 10th anniversary of his debut album,
Rappa Ternt Sanga, T-Pain performed a short set of some previous hits, along with a cover of "
A Change Is Gonna Come" and the premiere of a new song, "Officially Yours". On October 27, 2016, T-Pain premiered "Dan Bilzerian" (featuring
Lil Yachty). He worked with
Bruno Mars on his third studio album,
24K Magic, as one of the writers on the track "Straight Up & Down". After teasing the release of a long-shelved collaboration project with Lil Wayne,
T-Wayne was released on May 18, 2017, via T-Pain's
SoundCloud for streaming and free digital download. It consists of eight tracks recorded in 2009 described as "lost demos". In 2017, he collaborated with Italian rappers
J-Ax and
Fedez for the single "
Senza pagare", from the album
Comunisti col Rolex. After numerous delays and project name changes, T-Pain's fifth album
Oblivion was released November 17, 2017.
2019: 1UP On February 27, 2019, the same day T-Pain was revealed to be the winner of the
first season of
The Masked Singer, he released a surprise new album titled
1UP and announced a new U.S. tour in support of it. He hosted the
iHeartRadio Music Awards on March 14. In December 2020, T-Pain appeared in
ComplexLand virtual event to discuss his thoughts on the future of
esports.
2023–present: On Top of the Covers On March 17, 2023, T-Pain released
On Top of the Covers. The album includes a selection of
cover songs and notably did not include the use of autotune. He collaborated with
Meghan Trainor on the single "
Been Like This" from Trainor's sixth album
Timeless. In February 2024, T-Pain acknowledged that he had
ghostwritten music for
country singers including
Rhett Akins,
Luke Bryan, and
Dallas Davidson while living in
Nashville, Tennessee, for two years, but said that he preferred not to be credited on country songs because of the racism he experienced in the country music industry. == Other ventures ==