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6 years ago Drake and Giveon dropped “Chicago Freestyle,” a smooth and introspective standout from Dark Lane Demo Tapes, alongside “When to Say When.” “Chicago Freestyle” peaked inside the top 15 of the Billboard Hot 100 and blended Drake’s reflective verses with Giveon’s deep melodic hook. Its late night vibe helped both songs become some of the most replayed tracks from that era. #drake
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