Wale's debut studio album, Attention Deficit (2009) was under-shipped and thus underperformed commercially, but saw positive critical reception and spawned his first Billboard Hot 100 entry with its lead single, "Chillin" (featuring Lady Gaga).

He continued gaining mainstream recognition with his guest appearance alongside Roscoe Dash on Waka Flocka Flame's 2010 single "No Hands", which peaked at number 13 on the chart and received diamond certification by the Recording Industry Association of America (RIAA).

He then signed with Florida-based rapper Rick Ross' Maybach Music Group, an imprint of Warner Records the following year to release his second album, Ambition (2011).

Supported by the Grammy Award-nominated top 40 single "Lotus Flower Bomb" (featuring Miguel), the album saw further critical and commercial success, and peaked at number two on the Billboard 200.

[3][4][5][6] Folarin II marked his final album with Maybach Music Group, and he signed with Def Jam Recordings in the following year of its release.

[7][8] Olubowale Victor Akintimehin was born on September 21, 1984, in Northwest, Washington, D.C.[9] His parents were both from the Yoruba ethnic group of southwestern Nigeria and came from Austria to the United States in 1979.

[17] Manager Weisman told HitQuarters that the Fader feature, given the magazine's music/culture/fashion orientation, laid an important foundation for Wale to position himself as a "cool, smart, up-and-coming hip-hop artist who might be Drake".

[14] In January 2007, Wale released a new single to radio called "Good Girls" produced by Gerard Thomas and Demario Bridges for TeamMusicGroup (LeTroy Davis).

[27] He also appeared alongside Lupe Fiasco and Kardinal Offishall on Interscope label mate DJ Greg Street's single "Dope Boys" which samples Hip Hop classic T.R.O.Y..[28] On June 19, 2009, Wale released his fifth mixtape, Back to the Feature, on which eleven of the tracks were produced by 9th Wonder, with contributions also coming from Mark Ronson and others.

[29] The album's title, a play off the name of the movie Back to the Future, referred to the fact that a lengthy list of rappers joined Wale on the songs, including K'naan, Tamere Guess, Talib Kweli, Joell Ortiz, Beanie Sigel, Curren$y, J. Cole and Bun B.

[30] The mixtape received positive reviews from Vibe magazine[30] and website Pitchfork Media,[31] but Colin McGowan of Cokemachineglow commented that it represented neither "a step forward or back [for the artist] so much as shouting-in-place.

Other guest artists on the album included Pharrell Williams, Bun B, Chrisette Michele, K'Naan, Marsha Ambrosius, J. Cole, and Melanie Fiona.

[37] During this time, Wale was also in the studio with Gucci Mane, Waka Flocka Flame, Roscoe Dash, Sean Garrett, and Drumma Boy.

[40] More About Nothing creatively integrates sitcom material with rhyme and wordplay to present Wale's frustrations on his plight to reach mainstream acceptance and success.

Features include Wiz Khalifa, Waka Flocka, Daniel Merriweather, UCB, and Board Administration Artists Tiara Thomas, Black Cobain, and Fat Trel, as well as NBA Player and DC Native Kevin Durant.

On February 5, 2011, during Super Bowl XLV festivities, Wale announced his signing to artist Rick Ross' Maybach Music Group.

In 2009, Wale signed to Jay-Z's Roc Nation for management, along with other artists such as J. Cole, Mark Ronson, Melanie Fiona and Rihanna.

Later the same month, he confirmed pre-production efforts for Ambition, his second album, slated for a fall 2011 release under Maybach and Warner Music Groups.

[42] This marketing strategy was the brainchild of The Board Administration CEO Le'Greg O. Harrison and was executed through savvy social media integration, resulting in the first shut down of renowned file sharing site Hulkshare in the first 4 seconds of posting the link.

[46] On September 28, 2011, Wale revealed that Ambition was complete and released the single "Lotus Flower Bomb", featuring Miguel on Twitter.

[52] The never-seen-before element of Wale's Ambition promo blitz included a partnership formed between the current most popular file sharing site Hulkshare and The Board Administration.

[53] Later the same day, a private Ambition media listening event, held at the Gansevoort Hotel of Chelsea New York, was attended by music executives, bloggers, various artists, and hip hop heads.

[53] On November 2, 2011, Myspace and Hot 97 presented a complimentary Wale and friends midnight Ambition release show at The Highline Ballroom in New York City.

[60][61] The mixtape featured Rick Ross, 2 Chainz, Scarface, Nipsey Hussle, French Montana, Tiara Thomas, Lightshow, and Trinidad James, with production by Hit-Boy, Jake One, Cardo, Diplo, Beat Billionaire and Rico Love, among others.

When speaking of his third studio album Wale would say, "It's going to have one sound, very, very soulful", and said that the first single, "Bad", "is a pretty good indication of the direction I'm going for this project."

[70] The following month, it was revealed that Wale would next serve as the Executive Producer for Maybach Music Group's next collaborative album Self Made 4.

[71] He also recorded the original music theme for the popular ESPN sports talk show First Take, which features journalists/panelists Stephen A. Smith, Max Kellerman and moderator/host Molly Qerim.

After parting ways with Atlantic Records in February,[72] Wale released a surprise four-track EP titled It's Complicated on March 13, 2018.

[77] On September 14, he released a third EP titled Free Lunch, with guest appearances from singer Eric Bellinger and long time friend and collaborator, J.

[6][82] On October 20, 2023, it was announced publicly that Wale had left Maybach Music Group after falling out with label boss Rick Ross and signed with Def Jam Recordings.