Dupe Olaoye-Osinkolu was born in Lagos, Nigeria, on July 13, 1960, to the family of Chief Kareem Kehinde (K.K) and late Mrs. Olayinka Kehinde. Dupe, the first child, has five siblings. She began her career as a commercial dramatist in 1981, inspired by Dr. Laolu Ogunniyi, then Director of Programmes at the Broadcasting Corporation of Oyo State (BCOS) in Ibadan. She worked with the radio service and became a seasoned theatre artist, featuring in several films and television soaps, including Moses Olaiya (Baba Sala)'s "Aare Agbaye.

During her acting career, Dupe held several leadership positions within the Association of Nigeria Theatre-Arts Practitioners (ANTP):
- Osun State Public Relations Officer (1992-1994)
- National Welfare Officer (1995)
National Treasurer (1996-1997)

She also wrote the TV community drama series "Moriyina," which was adapted for NTA Ibadan in 1985 and aired during the popular 7 pm slot on Tuesdays for two quarters of 26 weeks. Her other dramatic works include:
"Better Days" by Laolu Ogunniyi
"Dinner of Death" (written by her, produced by NTA Ibadan)
"Eje Talaka" by Yemi Ogunyemi
"Ako Aja" by Wale Adeduro
"Ofin Foju" by Tai Arogunmatidi
"Gbekude," "Ogun Abele," "Karinkapo," "Iwe Irinna" by Tubosun Odunsi
"Alajopin" by Oyewole Olowomojuore
"Kuti Atiba" by Jide Alaba Are

Dupe transitioned from acting to journalism, becoming the Chairman of the Nigeria Association of Women Journalists (NAWOJ), Lagos Chapter, for two tenures from 2010 to 2016. During her leadership, she advocated for the elongation of maternity leave from three to six months and the provision of crèches in workplaces to support breastfeeding mothers.
She was also elected in absentia as Chairman, Labour Writers Association of Nigeria (LAWAN), 2006-2008, and Treasurer, LAWAN, 2004-2006. For four years, Dupe led the Save-the-Mothers' initiative, requesting the Lagos State Government to extend maternity leave during the Lagos NAWOJ Family Week, which she initiated in 2010. With a push by Hon. Tayo Oduntan and others, her efforts culminated in the 2014 signing of a bill by Governor Babatunde Fashola’s administration, extending maternity leave to six months with 10 days of paternity leave.