In the back of a white Jeep Wrangler Cousin Stizz stands, bare chested, wearing a gold chain and Red Sox camo snapback. “Shoutout to the money, love the drugs / Shoutout to the money from the drugs,” he raps. He’s riding around the streets of Boston with his friends, blunts in tow, the wind whipping through their hair, the sun beating down on their backs through the open roof: This was the first look most people got of the 23-year-old Boston rapper, in his video for “Shoutout.” “We just wanted to do something cool. We just wanted to show...

In the back of a white Jeep Wrangler Cousin Stizz stands, bare chested, wearing a gold chain and Red Sox camo snapback. “Shoutout to the money, love the drugs / Shoutout to the money from the drugs,” he raps. He’s riding around the streets of Boston with his friends, blunts in tow, the wind whipping through their hair, the sun beating down on their backs through the open roof: This was the first look most people got of the 23-year-old Boston rapper, in his video for “Shoutout.” “We just wanted to do something cool. We just wanted to show y’all...