Singer Tippu emerged as a charming, affable voice in Tamil film soundtracks at a time when musical experiments were on the rise in the early 2000s. Composers like A.R. Rahman, Mani Sharma, Harris Jayaraj and Devi Sri Prasad weaved more modern pop sounds into their OSTs, and Tippu was often the playful voice that reflected a track’s careless abandon and tender affection when it came to matters of love. The singer became synonymous with an entire generation of Tamil movie stars who were both macho and kind-hearted. Hear Tippu’s dynamic range in this playlist.