The teen rapper, who teamed up with Justin Timberlake's protégé Esmée Denters for current hit 'Until You Were Gone', is keen to tap into the Bajan hitmaker's popstar magnetism.
"I'd definitely like to work with Rihanna. I think she's beautiful but that's beside the point - I'm all about that swagger and she's got mad presence," he told Digital Spy.
"You want to watch her whether she's dressed up like GaGa or whether she's in her Caribbean gear. She's got a distinctive voice and she's roughly in my age category as well, so it wouldn't be an unnatural collaboration. She's golden."
Chipmunk, who released the 'Platinum Edition' of his debut album on Monday, also revealed that he will not be working with 'Until You Were Gone' producer Fraser T Smith on his follow-up LP - half of which he has already completed.
"I worked with him on the single and man, he's a hitmaker, but I've already got my team of producers for this album," he explained.
"There are three of us and that's all I need. They believe in me and my storytelling and we're going to work together to try and create a mindblowing album."
> Click here to read our brand new interview with Chipmunk