Rickey Smiley Talks Grief, Grace, & ‘Fool-ish’ (Interview)

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Photo Credit: Hollery Morris

🎤 The Return Of Rickey Smiley

After nearly 14 years without a stand-up comedy special, Rickey Smiley is making his long-awaited return with “Fool-ish,” premiering May 30 on Hulu.

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In our heartfelt and hilarious conversation, Rickey opened up about life, laughter, and legacy—and reminded us why he remains one of comedy’s most beloved voices.

💫 Coming Home With ‘Fool-ish’

Rickey didn’t just film his comeback special anywhere—he did it in Birmingham, Alabama, his hometown, at the historic Lyric Theater, just two doors down from the clothing store where he used to write jokes as a young dreamer.

I remember being in that clothing store, writing jokes… never would’ve thought two doors down I’d be shooting a comedy special 35 years later.

Performing at home came with extra pressure, though.

You better be funny. Ooky gon’ tell your auntie you wasn’t funny.

Somebody’s gon’ tell your mama. Your great-aunt. 

🎭 The Difference Between Funny & Stand-Up

Rickey dropped gems about the difference between being “funny” and being a real stand-up comedian, offering advice to anyone considering comedy.

You can be funny at Thanksgiving, but can you take that funny to the stage and make strangers laugh for an hour?

That takes years, commitment, and life experience.

He also got real about navigating today’s culture of sensitivity and cancelation:

If you wanna make everybody happy, sell ice cream.

💔 On Grief, God, and Giving Back

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Rickey opened up about the devastating loss of his son, Brandon, and how faith, service, and his book “Sideshow: Living With Loss and Moving Forward With Faith” helped him find purpose through pain.

You have to find ways to be okay. It’s all about the perspective you put things in—what window are you gonna look out?

He shared how continuing to serve others, even through his own grief, brought him healing:

While you’re over here doing good for somebody, God is over here working out your problem.

😂 The Iconic Characters & That Joe Willie Comeback

Yes, Miss Bernice Jenkins, Little Darryl, Precious and Her Grandmama, and a fan-favorite Joe Willie and the Deuteronomaires are all still in the mix!

I dress up like an old man in a fat suit and sing with a real gospel quartet… it’s the funniest thing I do now!

🧡 A Full-Circle Moment, 15 Years in the Making

In a vulnerable and powerful moment, Rickey graciously apologized for a long-ago misunderstanding during a media event that left me crushed as a new blogger.

Our honest exchange was filled with laughter, healing, and a promise for a proper do-over:

I’m gonna make sure you’re introduced properly… in a crowded room full of big ballers and shot callers.

Talk about full circle and divine timing.

📺 Watch The Full Interview

Trust me—this conversation is one you need to watch.

It’s raw, funny, emotional, and filled with purpose. Rickey’s transparency and grace will inspire you.

👉🏾 Watch the full interview now
👉🏾 Mark your calendar for Foolish on May 30
👉🏾 Grab a copy of Sideshow for healing and hope


📚 Resources & Must-Clicks


Will you be watching Rickey Smiley’s return with “Fool-ish”? Drop a comment and let’s talk about it!

2 COMMENTS

  1. Great interview. It is awesome how all Glory is given to God during difficult times. Rickey Smiley strength, endurance, and encouragement shows in this interview. I love that he apologized to you ( lol @ the black stockings and white shoes).

  2. It was great to hear about how he has dealt with grief and how you guys hash out the issue between each other. ❤

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