Smiling man holding a baby at event.

Rickey Smiley Walking Through His Wrap Party With His Granddaughter [VIDEO]

01/03/2024
Here’s Rickey Smiley and his granddaughter Denver greeting friends...
Comedy Special / Family & Friends / Videos
Young boy with closed eyes indoors.

Rickey Smiley’s Surprise Christmas Gift For His Grandson [VIDEO]

12/25/2023
This gift probably wasn’t on Grayson’s Christmas list!
Family & Friends / Videos
Smiling child standing near a wall.

Rickey Smiley’s Grandson Working Out [VIDEO]

12/23/2023
Grayson Smiley goes hard in the gym!
Family & Friends / Videos
Two people smiling in a car.

Top 5 Ms. Jannie Moments Of 2023 [VIDEO]

12/23/2023
Rickey Smiley and Ms. Jannie had some good times...
Best Of The Year / Family & Friends / Videos
Man dancing energetically on stage in suit.

Clap For Big Chris! [VIDEO]

12/21/2023
Here’s Big Chris doing the most after Rickey Smiley...
Family & Friends / Videos
Two men smiling in formal attire indoors.

Rickey Smiley Kickin’ It With Big Chris Before Karaoke Night [VIDEO]

12/20/2023
Here are Rickey Smiley and Big Chris in a...
Behind The Scenes / Family & Friends / Videos
Child running on a grassy field track.

Rickey Smiley Teaching His Grandson How To Run Routes & Catch Punts [VIDEO]

12/20/2023
Rickey Smiley’s grandson Grayson loves to play football and...
Family & Friends / Videos
Airplane flying against clear blue sky.

Rickey Smiley Flying Over His Momma’s House [VIDEO]

12/16/2023
Rickey Smiley told his mother he was flying over...
Family & Friends / Videos
Two men smiling by a Christmas tree.

Ghetto Christmas From The Smileys (2017) [VIDEO]

12/16/2023
This video still makes Rickey Smiley laugh.
Family & Friends / Videos
Two smiling men with beards.

Rickey Smiley Preparing For His Stand-Up Special With David E. Talbert [VIDEO]

12/14/2023
Rickey Smiley is about two weeks away from shooting...
Family & Friends / Live / Videos