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In this iconic throwback video from 1994, the legendary Tupac Shakur is seen enjoying a sunny day out on the streets of Los Angeles alongside acclaimed director John Singleton. During a walk for an episode of BET’s Rap City, Tupac’s playful and charismatic personality shines through when he notices a young boy standing on the sidewalk. With his signature humor, Tupac jokingly reacts to the little guy’s serious expression, creating a moment that is both lighthearted and memorable. The video has gained modern fame due to a popular internet theory suggesting the young boy is actually a toddler version of the artist Tyler, The Creator. While Tyler himself has since clarified with a laugh that it wasn’t him, the visual similarity—especially the striped shirt and cool hat—continues to make fans smile. It is a wonderful glimpse into Tupac’s ability to connect with people of all ages, showing his gentle and humorous side as he shares a quick, friendly interaction with his youngest “mean-mugging” fan.