We strongly encourage that all events adhere to COVID-19 safety guidelines. Possibly the most famous jazz trumpet player of all time, right behind Louis Armstrong, Miles Davis stands tall at #2 on our list of best jazz trumpet players. 3 Chicago, IL planners have requested price quotes from Trumpet Players in the last year. Review customized quotes and evaluate your options. Jeff Hedberg, BluJazz recording artist, is a 26-year-old jazz singer, flugelhorn and trumpet player. 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