Macklemore, Milano

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Macklemore — born Benjamin Hammond Haggerty in Seattle in 1983 — started rapping as a teenager and released his first EP under the name Professor Macklemore as early as 2000. For a decade he built himself up on Seattle’s underground scene with the solo debut The Language of My World (2005) and The Unplanned Mixtape (2009), but it was the collaboration with producer Ryan Lewis that changed everything. The duo’s self-released The Heist (2012) reached number two on the Billboard 200, and the singles “Thrift Shop” and “Can’t Hold Us” both topped the Hot 100 — a historic feat for independent artists. At the 2014 Grammy Awards they won four prizes, including Best New Artist and Best Rap Album. After the second album This Unruly Mess I’ve Made (2016), Macklemore returned to his solo career with Gemini (2017) and Ben (2023). Musically, Macklemore operates at the intersection of rap, pop and something approaching confessional literature. He has always been open about his own struggles — addiction, privilege, identity — and uses music as a tool for self-examination as much as entertainment. Songs like “Otherside” and “Starting Over” address substance abuse with a honesty that is unusual in the mainstream, while “Same Love” became a hymn for same-sex marriage. In 2024 he released the protest song “Hind’s Hall” in support of Palestinians, with all proceeds going to UNRWA — a move that confirmed his position as one of rap’s most politically outspoken voices. He has never been afraid to take a stand, even when it costs. Live, Macklemore is an unpredictable and generous entertainer — equal parts chaos and warmth. The concerts are energetic, often funny, and marked by an artist who genuinely enjoys standing in front of people. He has played to hundreds of thousands at festivals around the world, but retains something of the unpolished, almost amateur glow from his Seattle days. It is that combination — enormous reach with an underground foundation — that makes him an artist people still show up for.​​​​​​​​​​​​​​​​