Chicago Artist Annie Lee: Her Legacy Lives On

Annie Lee, an internationally-renowned artist and civil rights advocate, passed away 9 years ago on this day, but her legacy of iconic artwork depicting African American life lives on. Ever since she took the art world by storm during her first gallery show in 1985 – when her artwork sold out in just four hours – Annie Lee has been a central and celebrated figure in the industry.

Annie Lee grew up in Chicago and began painting at the age of 10. She was offered a four-year scholarship to attend Northwestern University after graduating from high school, but opted to marry and raise a family instead. While working at Northwestern Railroad as a chief clerk, Annie studied and sharpened her artistic skills at night, eventually earning a masters degree in Interdisciplinary Art from Loyola University. 

Painting at night became Annie’s haven and released her from the pressures of everyday life. While some pieces captured scenes she had personally witnessed, others portrayed her whimsical view of the world and the human experience. Art commentators even dubbed Annie’s style “Black Americana” for her realistic and humorous portrayals of historical and contemporary African American family life. 

Annie’s railroad job inspired “Blue Monday,” her most iconic painting.

Several of Annie’s paintings – such as My Cup Runneth Over – were widely-known. But it was her railroad job that inspired “Blue Monday.” This iconic piece depicts a woman struggling to get herself out of bed—and is likely a self-portrait of Annie (who used to wake up regularly at 5 AM to go to work). 

In fact, one of the hallmarks of Annie’s paintings are her faceless figures which allows viewers to mentally project and situate themselves in various scenes and perspectives. That’s why even though “Blue Monday” was created in the mid-80’s, it still resonates with people all over the world. Whether in response to the news, relationships, or moods, people have used this artwork in memes or social posts to convey their mentally, physically, and emotionally exhausted feelings. In December 2022, popular Rap singing star Lizzo too paid homage to Annie’s work by recreating it during her guest appearance on Saturday Night Live.

Click on image to enlarge.

Unfortunately, working so tirelessly and living in such close proximity to her paintings brought about new challenges for Annie. The fumes from the acrylic paints she used made her sick, and even worse, she developed spinal problems and tendinitis. Eventually, she stopped painting due to personal difficulties that included losing two husbands to cancer and her son to a tragic car accident. Annie took time off to grieve, and while doing so, decided it was time to take a leap of faith and capitalize on her talent full-time at the age of 40. She never returned to the railroad again.

She also became involved in humanitarian work and raised funds to help younger artists who attended historically Black colleges and universities.

Annie continued supporting Black excellence through other media, too. She became involved in humanitarian work and raised funds to help younger artists who attended historically Black colleges and universities. She also established herself as a respected and business savvy entrepreneur by developing a line of high fashion dolls and decorative home décor items recreated from her paintings so that anyone, on any budget, could own a piece of her art. 

Annie’s paintings have even been highlighted in television and movie sets such as “A Different World”, “227,” “Coming to America,” “ER,“Boomerang” and “Barber Shop,” and she also appeared in many major galleries, museums and notable private collections including those of of Will Smith, D.L. Hughley, and the late Arthur Ashe to name a few. 

Indeed, Annie is far from forgotten. So, today, we at FF2 Media recognize and revere Annie Lee for her outstanding ability to connect history, culture, and community through her artistry. Brava, Annie Lee!

© Reanne Rodrigues (11/14/14) Special for FF2 Media

Visit the Annie F. Lee Art Foundation website here.

Visit Annie Lee’s Wikipedia page.

Read more about Lizzo’s tribute to Annie Lee on Saturday Night Live here. 

Images courtesy of Reanne Rodrigues & used with her permission.

Lizzo image cropped from her Instagram site. Read more about Lizzo’s tribute to Annie Lee on Saturday Night Live here.


We reached out to everyone we could think of for authorized images of Annie Lee’s enormous output of paintings and sculptures, but we got no response. That said, a fabulous array of merch is available everywhere including Amazon, eBay, Etsy, & the Annie Lee Gifts site. We also reached out to Lizzo, but got no response. So, we did our best to do what we could…

If you represent either Annie Lee or Lizzo, please get back to us. We respect intellectual property rights, and we always strive for compliance.

Tags: Annie Lee, HBCUs, Historically Black Colleges/Universities, Lizzo, Reanne Rodrigues, Saturday Night Live

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Reanne is an arts and culture writer based in Manhattan, New York City. She loves telling impactful stories about artists and the value they bring to the world. Reach out to her if you’d like to collaborate on any projects or indulge in a lively discussion over chai at
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