Through the latter half of the '80s into the next decade, Winans recorded several award-winning albums, and they regularly reached the Top Ten of Billboard's gospel chart. The material ranged from deeply gospel to contemporary Christian and often mixed the approaches. Her most popular songs from the period include "Daddy Can't Sing," "First Trumpet Sound," "The Diet Medley," "Boyfriends," "Its Yo Thang," "Give It One More Try," "Sweeter Than the Honeycomb," and "Little Timmy." When she wasn't in the recording studio, she spent much of her time performing and often worked 200 nights each year. She also made numerous television appearances on shows like Oprah, the Grammy Awards, Arsenio Hall, Queen Latifah, and The Pat Sajak Show and starred in Broadway musicals like Don't Get God Started.
Winans remained active during the 2000s and 2010s, a period during which she recorded for CGI, Verity, and her own label, Destiny Joy. Bringing It All Together (featuring collaborations with her son Mario Winans; 2003), Woman to Woman: Songs of Life (2006), and the Grammy-nominated How I Got Over (2009) all topped the gospel chart. Winans also put together a handful of comedic releases. ~ Charlotte Dillon, Rovi