He went to Robert Morris College and Virginia State University on football scholarships, and then Bowie State University but dropped out in 2004 to pursue music full-time. Before music became a viable source of income, Wale worked day jobs at Sprint, Up Against The Wall and Downtown Locker Room.
"Dig Dug (Shake It)" became popular in Washington, D.C., Maryland and Virginia. It was also very popular in eastern North Carolina. The song became the most requested song by a local artist in D.C. radio history and Wale was the first local artist to get any BDS spins since DJ Kool in the early 1990s. The song was included in Wale's first mixtape, Paint a Picture.
In July 2006, Wale hired Daniel Weisman, a former club DJ and promoter, as his manager. In September 2006, after dropping another go-go influenced single, "Breakdown", sampled from Huck-a-Bucks "Sexy Girl", and a mention in The Washington Post. Wale released his first non-go-go original single, "Uptown Roamers." On Thursday September 14, 2006, "Uptown Roamers" debuted on XM Radio Channel 66 and was played twice in one day. Both "Breakdown" and "Uptown Roamers" were on Wale's second mixtape, Hate Is the New Love.
In October 2006, Wale debuted three ringtones and two wallpapers on Jamster and performed at Howard Homecoming at Howard University, where he caught the eye of Def Jam A&R and Jay-Z's engineer, Young Guru. Later in October 2006, Wale, performed at Bowie State University in Bowie, Maryland for their homecoming concert.
In November 2006, a feature ran on AllHipHop.com's Breeding Ground about Wale. The day before Thanksgiving, Wale took the stage between Lil Wayne and T.I. during the Southern Invasion tour at the Verizon Center.
In early December 2006, Wale won the award for "D.C. Metro Breakthrough Artist of the Year" at WKYS' Go-Go Awards . On December 15, The Fader magazine associate editor Nick "Catchdubs" Barat visited Wale for an interview and photo shoot which appeared in the March 2007 issue of The Fader.
Wale has an upcoming promotional campaign with Remy Martin and XXL Magazine. He has also been linked to boutique streetwear brands The Hundreds, 10 Deep and Good Bully, as well as lifesyle brands Stussy and LRG.
Wale often has prominent go-go band UCB join him for his shows.
Wale released his third mixtape, 100 Miles & Running, on July 11, 2007 as a free download on his myspace page. To date, the mixtape has been downloaded over 30,000 times. This mixtape includes features from Mark Ronson, Daniel Merriweather, Amy Winehouse, and Lily Allen. It was released on the same day as his performance at the Highline Ballroom, in Manhattan. The Highline show was to promote the US release of Mark Ronson's album and included performances by Mark Ronson, Wale, Saigon, and Daniel Merriweather. Jay-Z, Beyonce, Kanye West, Maroon 5, Clive Davis, Eve and Danny Masterson were all in attendance. There, Wale was interviewed by MTV News correspondent J.D. Tuminski for his first national TV feature, which was released on August 16, 2007.
Wale was also featured in the October 2007 issues of XXL and Rolling Stone . The Washington Post profiled Wale on the front page of the Sunday Style section in the October 21st, 2007 edition. Wale is featured on the cover of URB's 150th issue along with French electro group, Justice.
iTunes released "Nike Boots" as a free download on November 13th, 2007 as its "Single of the Week." On Christmas Day 2007, Wale debuted the "Nike Boots Remix" featuring Lil Wayne and Green Lantern on his myspace page. Wale and Lil Wayne played a Nike Boots event called DC Stand Up at Ibiza Nightclub in DC on January 15, 2008 which was sponsored by Nike and Footaction.
On February 1, 2008, Wale launched a website with his manager called Elitaste.com.
On April 29, 2008, the new Roots album, titled Rising Down, was released. Wale was featured on the song "Rising Up" along with Chrisette Michele. Wale's relationship with the Roots began when Black Thought heard a song recorded as a tribute to him on Wale's 100 Miles & Running mixtape and contacted Wale.
On May 30, 2008, Wale released his 4th mixtape, The Mixtape About Nothing, for free through www.elitaste.com and 10deep.com in collaboration with the streetwear brands Commonwealth and 10 Deep. 10 Deep also be releasing the "Serenity Now" tee in collaboration with Wale's release of this mixtape. Everyone who purchased the "Serenity Now" tee also received a hard copy of The Mixtape About Nothing. The majority of the mixtape was produced by DC's Best Kept Secret.
In the June issue of the German Hip-Hop magazine JUICE Wale announced that his upcoming debut-album will feature production credits from Mark Ronson, Kanye West, Just Blaze, 9th Wonder and the French electronic music duo Justice.
In the June/July 2008 issue of Giant Magazine, Wale announced he is making a new mixtape called Back to the Feature, which will be produced by 9th Wonder. This will be coming out at the end of September 2008
In a recent interview with Washington Post's Express, Wale announced that he was recording a song with Chrisette Michele called "Shades" for his upcoming album, which discusses inter-black racism. Wale also said content like in The Mixtape About Nothing will be on the album.
In a Elitaste interview, Young Chris said about Wale, "We’re ready to do a mixtape together; we ain’t got the name nor the DJ yet, but we’ve had some good talks and we’ll get that mixtape out.
Wale stopped into Travis Barker’s studio in August 2008 to lay down a verse for Travis’ solo album, Travis then laid down some live drums on a Wale album cut, “G Told Me” produced by Sean C & LV (”Roc Boys”).
On October 9, Wale announced that he was going to shoot a video for "Nike Boots." He did not state if Nike Boots was going to be rereleased as a single off of his upcoming album or not. The same day, Wale released a remix of M.I.A.'s song "Boyz" via the Elitaste website.