input: Smith graduated from Hampshire College in Amherst, Massachusetts in 1991 with a degree in philosophy and political science. "Went straight through in four years", he explained to Under the Radar in 2003. "I guess it proved to myself that I could do something I really didn't want to for four years. Except I did like what I was studying. At the time it seemed like, 'This is your one and only chance to go to college and you had just better do it because some day you might wish that you did.' Plus, the whole reason I applied in the first place was because of my girlfriend, and I had gotten accepted already even though we had broken up before the first day." After he graduated, he "worked in a bakery back in Portland with a bachelor's degree in philosophy and legal theory". While at Hampshire, Smith formed the band Heatmiser with classmate Neil Gust. After Smith graduated from Hampshire, the band added drummer Tony Lash and bassist Brandt Peterson and began performing around Portland in 1992. The group released the albums Dead Air (1993) and Cop and Speeder (1994) as well as the Yellow No. 5 EP (1994) on Frontier Records. They were then signed to Virgin Records to release what became their final album, Mic City Sons (1996). Around this time, Smith and Gust worked a number of odd jobs around Portland, including installing drywall, spreading gravel, transplanting bamboo trees, and painting the roof of a warehouse with heat reflective paint. The pair were also on unemployment benefits for some time, which they considered an "artist grant". Smith had begun his solo career while still in Heatmiser, and the success of his first two releases created distance and tension with his band. Heatmiser disbanded prior to the release of Mic City Sons, prompting Virgin to put the album out inauspiciously through its independent arm, Caroline Records. A clause in Heatmiser's record contract with Virgin meant that Smith was still bound to it as an individual. The contract was later bought out by DreamWorks prior to the recording of his fourth album, XO.

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input: In 2007, T-Pain began work on his third album with Rocco Valdes, Akon and Lil Wayne. The album was also his first under his Nappy Boy Entertainment. T-Pain's third studio album, Thr33 Ringz, was released on November 11, 2008. The album sold 168,000 records in its first week, reaching number four on the Billboard 200. A mixtape, Pr33 Ringz, was released in early 2008 before the album. The album was preceded by three singles. Its lead single, "Can't Believe It", featuring Lil Wayne, was released in July 2008. The single 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. The single reached number twenty-seven 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 and reached number thirty-eight on the Hot 100 and number thirty-nine on the Hot R&B/Hip-Hop Songs chart. Guest appearances on Thr33 Ringz included T.I., Lil Wayne, Ludacris, DJ Khaled, Ciara, Chris Brown and Kanye West among others. Pr33 Ringz was the introduction mixtape for the album. In 2008, T-Pain continued to appear on numerous rap 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 with Kanye West. 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 (on the episode hosted by Bradley Cooper with musical guest TV on the Radio) in the SNL Digital Short. T-Pain also supported the album in 2009 with his Thr33 Ringz Tour, which included sold out shows across North America. T-Pain and rapper 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. In 2009, T-Pain hosted the BET Awards afterparty and paid tribute to Michael Jackson in West Covina.

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In 2007, T-Pain began work on his third album with Rocco Valdes, Akon and Lil Wayne.