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Bring half-and-half to a simmer in a medium saucepan over medium-high heat. Whisk in chocolate, sugar, and cocoa powder and cook, whisking frequently, until mixture is smooth and creamy and chocolate is melted, about 5 minutes. Remove from heat and whisk in vanilla and salt; chill at least 1 hour.
Pour chocolate mixture into ice-pop molds. Cover and insert sticks. Freeze until solid, at least 4 hours. Dip molds briefly in hot water to release pops.
Do Ahead: Chocolate mixture can be made 1 day ahead; keep chilled. Fudgecicles can be made 1 week ahead; keep frozen.