Delois Dean, known as Comedian DeeDee, is a multi-talented entertainer and entrepreneur with a passion for making people laugh, look good, and feel secure. As a comedian and host of her business LIPFE (Live It with a Purpose and Fabulously Everyday) Entertainment, DeeDee brings infectious energy and sharp wit to every stage, keeping audiences engaged with humor that’s both relatable and unforgettable.
She has graced stages like the House of Blues, Riddles Comedy Club, Vybez, Toni’s Gaming Parlor, The Artist Ground, and more. DeeDee has also hosted major events like the Association Chicago Galas and The Black Renaissance Fashion Show.
When not behind the mic, DeeDee is a full-time single mom to three amazing children, Vice President of Obey Your Dreams, working alongside CEO Mike Lawry Baby, and an Advocacy Coordinator Team Specialist for Sedgwick, a role she’s held for nearly 9 years.
She’s also a skilled loctician, helping clients embrace their natural beauty through expert loc care, a dedicated life insurance broker providing families with financial protection, and a talented bartender serving up handcrafted drinks and great conversation.
Whether she’s being a mom, working her 9-5, performing on stage, doing hair, securing families, or mixing the perfect cocktail, DeeDee is all about bringing joy, confidence, and peace of mind to everyone she encounters.
What are some major achievements or accolades that you’ve accumulated?
Some major achievements I’ve accumulated include hosting at iconic venues like the House of Blues and Riddles Comedy Club. I also won a comedy show that featured several talented comedians, and now I’ve been invited to perform at Uptown Comedy in Atlanta on May 22nd—which is a huge milestone in my career!
How do you use your platform as an influencer to spread what’s good to the world and who have you impacted?
Losing my husband to suicide shattered me in a way I never imagined possible. It was like the ground disappeared beneath me, and I was left to navigate a world with my children that suddenly felt unfamiliar, empty, and unbearably quiet. The pain was deep—not just because I lost the man I loved, but because I was left with so many unanswered questions, so much guilt, and a heartbreak that didn’t come with a roadmap. I use my platform to spread positivity, laughter, and realness—because the world’s already heavy, and sometimes people just need a reason to smile. Through my comedy, I highlight everyday situations we all relate to, and that shared laughter brings people together.
I also promote messages around self-confidence, unity, and mental wellness, especially in underrepresented communities.
I’ve impacted young and older creatives who tell me they’ve found the courage to chase their own dreams after watching me stay consistent in mine. I’ve worked with schools like Harold Washington Elementary and youth programs to host uplifting events. I also give shout-outs to small businesses and causes that deserve more eyes on them. Whether it’s through helping them promote content, a hosting gig, or a motivational post—my goal is to leave people better than I found them.
What are some projects that you are currently working on or promoting?
I’m currently promoting skits with real-life stories in collaboration with Nelly Nails World. I’m doing a mix of stand-up and storytelling that highlights everyday life with a twist.
I’m also building my brand as a host, collaborating with event organizers for weddings, corporate gigs, and festivals across the region. Additionally, I’m working with CEO Mike Lawry Baby on growing Obey Your Dreams into a worldwide movement, helping people manifest their dreams into reality.
Who do you have to credit for your success?
First, I want to thank God for giving me the strength to keep going. I also want to thank Nelly Nails World for encouraging me to step into comedy and turn my pain into purpose. And most importantly, I thank my children for believing in my vision and always being there for me.
What is your ultimate goal in your career/life?
My ultimate goal is to inspire, uplift, and leave a lasting impact. Whether I’m on stage, behind the chair, or just having a conversation, I want people to walk away feeling better, more confident, and more hopeful than before. I want to show people—especially women and single parents—that you can juggle it all and still shine. Oh—and don’t forget, I’m also a viral actress with over 20 million views across all platforms. So this is just the beginning!
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