Wright's father died when his son was only a year old. The future actor was raised by his mother—a lawyer for the US Customs Department—and his aunt, a nurse. Though he grew up in a black neighborhood in DC, Wright commuted across town to the elite, overwhelmingly white St. Albans School for Boys. (He drew upon this experience for his sensitive interpretation of Basquiat as a brilliant young black artist adrift and simmering in the treacherous white art world.) A political science major at Amherst, Wright intended to follow in his mother's footsteps but was bitten by the acting bug late in his college career. He has barely looked back since.

Prior to his Broadway triumph, Wright had worked at the Arena Stage in Washington, DC, the Yale Rep in New Haven, Connecticut and in regional theater. He subsequently played The Fool (as a crazed homeless man) to F. Murray Abraham's "King Lear" (1996). This led director George C Wolfe to cast him as 'da Voice', the highly entertaining narrator of the acclaimed tap-dancing Broadway musical "Bring in 'Da Noise, Bring in 'Da Funk" later that year. Wright has also played small parts in several features ("Presumed Innocent" 1990; "Jumpin' in the Boneyard" 1991) and on TV. One of his larger TV assignments was playing celebrated jazz musician Sidney Bechet, aloof and dignified, on two feature-length installments of "The Young Indiana Jones Chronicles" in 1993.

Wright continued to work steadily in film and television for the next several years, including a role in Woody Allen's "Celebrity" in 1998 and Ang Lee's independent film "Ride with the Devil" in 1999. He had a supporting role in the 2000 remake "Shaft" with Samuel L. Jackson and played Martin Luther King in the telepic "Boycott" in 2001. Also in 2001, Wright began performing in the Public Theater production of "Topdog/Underdog." Playing a career street hustler living with his younger brother, Wright received rave reviews in his performance opposite Don Cheadle. The play soon moved to Broadway where Cheadle was replaced by Mos Def and reviews marveled at the energy between Wright and Mos Def, saying the two actors played off each other like real brothers.

The momentum of his stage performance spilled into his film career as Wright went on to a supporting role as a bartender taking up with a mom (Ellen Barkin) whose daughter (Monica Keena) plots to murder her drunken stepfather (Michael Ironside) in the dreary “Crime and Punishment in Suburbia” (2000), a modern take on Fyodor Dostoyevski’s classic novel. After a role as the Gravedigger in a contemporary version of “Hamlet” (2000), starring Ethan Hawke as the anguished son of Denmark Corporation’s CEO whose ghost appears to demand vengeance for his murder most foul, Wright landed the part of Howard Bingham in 2001's "Ali" starring Will Smith. Wright reprised his stage role for a television miniseries version of "Angels in America," appearing with Al Pacino and Meryl Streep, which aired on HBO in 2003 and earned the actor an Emmy as Outstanding Supporting Actor in a Miniseries or a Movie, and a Golden Globe for Best Performance by an Actor in a Supporting Role in a Series, Mini-Series or Motion Picture Made for Television.

A small role in the straight-to-video crime thriller “Detox” (2002) was followed by narrating the Civil Rights documentary “With All Deliberate Speed” (2004), a look at how Brown v. Board of Education failed to stem discrimination because many districts continued under-funding schools in African-American communities. After a short, but unnerving performance as Cpl. Al Melvin in Jonathan Demme’s disappointing remake of “The Manchurian Candidate” (2004), Wright played Small Paul, a soft-spoken history buff who is rumored to have killed someone, in “Lackawanna Blues” (HBO, 2005), an autobiographical drama based on Ruben Santiago-Hudson’s Obie award-winning play about his growing up in a boarding house run by a woman (S. Epatha Merkerson) who became the caregiver of lost souls.

Then in Jim Jarmusch’s “Broken Flowers” (2005), Wright had a supporting role a crime-novel enthusiast who fancies himself a detective and convinces his neighbor (Bill Murray) to go on a road trip after being shown a letter from an ex-girlfriend claiming to be the mother of his long-lost son. He next appeared in M. Night Shaymalan’s critically-maligned fantasy, “Lady in the Water” (2006), playing a delusional tenant of an apartment building where a water nymph (Bryce Dallas Howard) suddenly appears in the pool. In danger of being killed by demon-like creatures from her mysterious water world beneath the pool, the nymph tries to get back to her world with the help of the building’s superintendent (Paul Giamatti) and its motley residents.

Wright next joined an excellent supporting cast in “Casino Royale” (2006), the 21st installment of the never-ending James Bond series and the first to star blonde Daniel Craig, whose cold and calculating take on Ian Fleming’s super agent hit closer to the author’s original vision of the character. Wright played Felix Leiter, a CIA mole who—along with MI6 operative Mathis (Giancarlo Giannini)—helps Bond take down a banker for terrorists (Mads Mikkelsen) in a high-stakes card game in Montenegro. Anticipation was high prior to the film’s November 2006 release, with most critics agreeing that “Casino Royale” was one of the best in the series.