2004–2018: Theatre roles and acclaim
In the early 21st century, Rashad was the first black actress of any nationality to win the Best Actress (Play) Tony Award, for her 2004 performance as Lena Younger in a revival of the play A Raisin in the Sun by Lorraine Hansberry. Rashad also won the 2004 Drama Desk Award for Best Actress in a Play for A Raisin in the Sun, tying (split award that year) with Viola Davis for the play Intimate Apparel. Rashad was nominated again for a Tony the following year, for her performance in Gem of the Ocean. In 2007, Rashad made her directorial debut with the Seattle Repertory Theatre's production of August Wilson's Gem of the Ocean. In 2008, Rashad starred on Broadway as Big Mama in an all African-American production of Tennessee Williams's Pulitzer Prize-winning drama Cat on a Hot Tin Roof, directed by her sister Debbie Allen. She appeared alongside stage veterans James Earl Jones (Big Daddy) and Anika Noni Rose (Maggie), as well as film actor Terrence Howard, who made his Broadway debut as Brick.
Rashad played "Kill Moves"' wealthy mother on the Chris Rock created sitcom Everybody Hates Chris on December 9, 2007. In 2007 she appeared as Winnie Guster the mother of main character Burton "Gus" Guster in the Psych episode "Gus's Dad May Have Killed an Old Guy". She returned to the role in 2008, in the episode "Christmas Joy". In February 2008, Rashad portrayed Lena Younger in the television film adaptation of A Raisin in the Sun, directed by Kenny Leon. It starred core members of the cast of the 2004 Broadway revival at the Royale Theatre of Lorraine Hansberry's 1959 play, including Audra McDonald as Ruth Younger, and Sean Combs as Walter Lee Younger. The television film adaption debuted at the 2008 Sundance Film Festival and was broadcast by ABC on February 25, 2008. According to Nielsen Media Research, the program was watched by 12.7 million viewers and ranked No. 9 in the ratings for the week ending March 2, 2008.
In 2009, she appeared as Violet Weston, the drug-addicted matriarch of Tracy Letts's award-winning play August: Osage County, at the Music Box Theatre. Rashad returned to directing August Wilson's work in early 2014, when she led a revival of Wilson's Fences, at the McCarter Theatre in Princeton, New Jersey. It received generally positive reviews. She continued to focus on Wilson's work, including a well-received production of Ma Rainey's Black Bottom, which she directed at the Mark Taper Forum in Los Angeles in late 2016. From March 17 to May 1, 2016, Rashad played the lead role of Shelah in Tarell Alvin McCraney's play Head of Passes at The Public Theater. Her performance was positively reviewed. In November 2010, Rashad featured as Gilda in the ensemble cast in the Tyler Perry film For Colored Girls, based on the play For Colored Girls Who Have Considered Suicide When the Rainbow Is Enuf by Ntozake Shange. Rashad said about this work in an interview with Vibe Movies & TV in 2010: "I saw the original Broadway play. I thought it was amazing how such a story that wasn't pretty was poetry. Usually poetry is about lofty things and this was the poetry of speech and the movement of everyday people. I found a little bit of it off-putting to tell you the truth, because it was so angry when I saw it. And I think Tyler Perry has added an element here that wasn't in the original stage production, and that is the necessity for taking responsibility for one's own self otherwise you are just living to die. That is where he wrote the line [in the film], 'You gotta take some responsibility in this. Otherwise you are just living to die.'"
In 2012, she starred in another Tyler Perry film, Good Deeds. Also in 2012, Rashad played Clairee Belcher in the remake of Steel Magnolias (the role originated by Olympia Dukakis). This version has an all African American A-list cast, including Queen Latifah as M'Lynn, Jill Scott as Truvy, Condola Rashad as Shelby, Adepero Oduye as Annelle, and Alfre Woodard as Ouiser. In 2015, she played Mary Anne Creed in the sports film Creed (2015), and again in the sequels Creed II (2018) and Creed III (2023). In 2016, Rashad was cast as a recurring guest star in the role of Diana DuBois in the third season of the Lee Daniels-produced Empire television series on Fox. In 2017, Rashad portrayed Bishop Yvette A. Flunder, pastor of The City of Refuge Church in San Francisco, Calif., as part of the Dustin Lance Black mini-series When We Rise. Her appearance in the show highlighted the reputed compassion of the church, the commitment of its leadership, and the loving home the church provides to minister in the tough, primarily African-American community in San Francisco.