Vibe magazine ranked a list of 77 of Lil Wayne's songs from 2007 and ranked his verse in DJ Khaled's "We Takin Over" as his best of 2007, with "Dough Is What I Got" (a freestyle over the beat of Jay-Z's "Show Me What You Got") from Da Drought 3. At the end of 2007, an MTV poll selected Lil Wayne as "Hottest MC in the Game", The New Yorker magazine ranked him "Rapper of the Year", and GQ magazine named him "Workaholic of the Year". In 2008 he was named "Best MC" by Rolling Stone. Another article, built around Lil Wayne's 2007 mixtape work, cites his creative practice as an example of post-performance creative practice.
Tha Carter III was released on June 10, 2008, with first-week sales of over 1 million copies, the first to do so since 50 Cent's The Massacre (2005). The album's first single "Lollipop", featuring Static Major, became the Carter's most successful song at the time, topping the Billboard Hot 100 and becoming his first top 10 single as a solo artist and his first number one on the chart. The third single "Got Money", featuring T-Pain, peaked at number 13 on the Billboard 100. Tha Carter III went on to win four Grammy Awards, including best rap album and best rap song, which he won for "Lollipop". On July 14, 2008, the Recording Industry Association of America certified Tha Carter III two times platinum. In October 2008, Lil Wayne announced plans to MTV News to re-release the album with new tracks, including a duet with Ludacris and remixes of "A Milli".
In 2008, Carter performed at the Voodoo Experience in October in New Orleans, which was described by Jonathan Cohen of Billboard as his biggest hometown headlining set of his career. He also performed at the Virgin Mobile Music Fest with Kanye West, where they performed the remix of "Lollipop" and lip-synced to Whitney Houston's "I Will Always Love You". Lil Wayne also performed at the 2008 MTV Video Music Awards with Kid Rock ("All Summer Long"), Leona Lewis ("DontGetIt (Misunderstood)") and T-Pain ("Got Money") and performed "Lollipop" and "Got Money" on the season premiere of Saturday Night Live. He later performed at the homecoming rally at Vanderbilt University and the 2008 BET Hip Hop Awards, where he received 12 nominations. He won eight awards at the BET Hip Hop Awards, one of which included the "MVP" title. After M.I.A. dropped out of performing on the I Am Music Tour due to her pregnancy, Jay-Z performed "Mr. Carter" with Lil Wayne at select shows.
Following Tha Carter III's achievement of selling over 3 million copies, becoming 2008's best-selling record, Carter re-signed with Cash Money Records for a multi-album deal. On November 11, 2008, Carter became the first hip hop act to perform at the Country Music Association Awards, playing "All Summer Long" alongside Kid Rock, in which Carter inaudibly strummed guitar strings alongside the guitarist in Kid Rock's band. Shortly after, Wayne was nominated for eight Grammys – the most for any artist nominated that year. He was then named the first MTV Man of the Year at the end of 2008. He won the Grammy Award for Best Rap Solo Performance for "A Milli", Best Rap Performance by a Duo or Group for his appearance in T.I.'s single "Swagga Like Us", and Best Rap Song for "Lollipop". Tha Carter III won the award for Best Rap Album. MTV News listed Carter number two on their 2009 list of the Hottest MCs In The Game.
Carter has announced several possible upcoming projects, including a collaborative album entitled I Can't Feel My Face with Harlem-based rapper Juelz Santana, that has been in production for several years. On June 19, 2008, Carter and T-Pain formed a duo called T-Wayne with plans to release an album, titled He Raps, He Sings; however, those plans have died down due to much of the material recorded for the album being leaked. T-Pain released T-Wayne in 2017. According to an interview with Drake, in the December 2011 issue of XXL, plans for an upcoming album with Carter had been scrapped for the time being because of the Jay-Z and Kanye West collaboration album Watch the Throne (2011).
His second child, Dwayne III, was born on October 22, 2008, at The Christ Hospital in Cincinnati to radio broadcaster Sarah Vivan. His third child, Cameron, was born to actress Lauren London on September 9, 2009. His fourth child, Neal, was born on November 30, 2009, to singer Nivea. Trina also became pregnant with Carter's child, but later suffered a miscarriage.
On September 24, 2008, Carter published his first blog for ESPN in their issue, ESPN The Magazine. Carter revealed he was a fan of tennis, the Green Bay Packers, the Boston Bruins, the Los Angeles Lakers and the Boston Red Sox. To commemorate the Packers' making it to Super Bowl XLV, he spoofed Wiz Khalifa's hit song "Black and Yellow" (which were the colors of the Packers' opponents, the Pittsburgh Steelers) in a song titled "Green and Yellow". Carter has continued writing for ESPN, notably reporting at the ESPN Super Bowl party. Carter made his debut on ESPN's daily sports round table show Around The Horn on February 10, 2009. Carter now currently sings the intro song "No Mercy" for the Fox Sports 1 sports debate show Undisputed.
On February 19, 2008, Carter and Cortez Bryant revisited their alma mater McMain Secondary School to get students to design an invitation to the gala introducing Carter's nonprofit One Family Foundation.
On January 23, 2008, Carter was arrested alongside two others. His tour bus was stopped by Border Patrol agents near Yuma, Arizona. A K-9 Unit recovered 105 grams (3.7 oz) of marijuana, almost 29 grams (1.0 oz) of cocaine, 41 grams (1.4 oz) of ecstasy, and $22,000 in cash. Carter was charged with four felonies: possession of narcotic drug for sale, possession of dangerous drugs, misconduct involving weapons and possession of drug paraphernalia. He was granted permission to travel outside of the state and remain out of custody on the $10,185 bond he posted.
On May 6, 2008, Carter returned to court in Arizona to plead not guilty to the charges. A bench warrant was issued on March 17, 2010 when Carter did not show for a final trial management conference. However, the rapper was already incarcerated, serving a one-year sentence in Rikers Island on weapons charges. On June 22, 2010, Carter pleaded guilty to the charges. As part of the plea deal he was able to serve 36 months of probation, which he was sentenced to on June 30, 2010.
On July 24, 2008, Abkco Music Inc filed a lawsuit against Carter for copyright infringement and unfair competition, specifically referring to Tha Carter III's track "Playing with Fire". In the lawsuit, Abkco says that the song was obviously derived from The Rolling Stones' "Play with Fire", to which Abkco owns the rights. Subsequently, "Playing with Fire" was removed from the track list of Tha Carter III on all online music stores and replaced with the David Banner produced track, "Pussy Monster".