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When Macklemore found fame in the early 2010s, he did so swaggering through Goodwill aisles in a tiger-print fur coat. His 2012 earworm “Thrift Shop” — built around a jaunty saxophone hook with the famous refrain “I’m gonna pop some tags / Only got $20 in my pocket” — was completely inescapable. It spent six weeks at number one on the U.S. Billboard Hot 100 Chart, and won him a Grammy Award for Best Rap Song, Rap Performance and Best Rap Album for The Heist, beating out Kendrick Lamar’s good kid, m.A.A.d city in the latter category. Macklemore had other major hits — most notably the high-energy locker-room anthem “Can’t Hold Us” and the socially conscious “Same Love” — but none quite matched the cultural ubiquity of “Thrift Shop”. It seemed as though he was destined to be synonymous with the cringe of 2010s pop culture (a fever dream defined by LMFAO’s “Party Rock Anthem” and Carly Rae Jepsen’s “Call Me Maybe”), and unable to break into the 2020s mainstream.
That was until last week, when the rapper found himself at the center of an international controversy after he was dropped from Ed Sheeran’s U.S. stadium tour over his onstage calls for a “free Palestine.” Macklemore had told the crowd that he wanted the people of Gaza and “the occupied West Bank” to know “we have not forgotten about them.” His comments were branded hateful by Gillette Stadium owner Robert Kraft and organizations including the Israeli-American Council and the Anti-Defamation League, which called them “completely unacceptable” and accused the rapper of antisemitism. Kraft told Sheeran the show would be cancelled if Macklemore remained on the bill. So he went.
The reaction was fierce, prompting figures from across the music industry and beyond to rally around Macklemore. All of Sheeran’s support acts, including Finneas, Aaron Rowe and Lukas Graham, dropped out of upcoming dates on the U.S. tour. Greta Thunberg, Bernie Sanders, New York Rep. Alexandria Ocasio-Cortez, Swedish popstar Zara Larsson, Hacks star Hannah Einbinder and Irish hip-hop trio Kneecap are among those to have spoken out in support of the rapper. More than a decade on from “Thrift Shop,” the guy who was singing about rocking your granddad’s clothes in 2012 has become an unlikely face of the Free Palestine movement.
Macklemore has only doubled down as the media storm surrounding Sheeran’s tour has waged on. On Thursday, he announced a “Free Palestine” concert tour in Dublin, Paris and London for October, with all proceeds going to organizations supporting Palestinians. He donated his $1 million earnings from his two dates on Sheeran’s tour to those organizations, and urged Kraft to match his donation. At the time of the performance, the Palestinian death toll had surpassed more than 73,000, according to Gaza’s Health Ministry. The United Nations has said that Israel’s actions in Gaza constitute genocide, but the country and its allies, including the United States, have denied this.
But Macklemore’s support for Palestine did not begin with the fallout from Sheeran’s tour. The rapper, whose real name is Benjamin Hammond Haggerty, has used his platform to speak out on the conflict since the October 7 attacks, including by signing a petition created by Artists4Ceasefire.
During Sheeran’s show at New Jersey’s MetLife Stadium, Macklemore told the audience that one of his main motivations for doing the tour was to share his message. “A big part of the reason why I wanted to do this tour in the first place is so I could stand up in stadiums like this and say two words that are very near and dear to my heart: Free Palestine,” he said on stage. In 2024, he released the song “Hind’s Hall,” inspired by the Columbia University protesters who unfurled a banner over the academic building Hamilton Hall to name it “Hind’s Hall” in tribute to a six-year-old Palestinian girl called Hind Rajab, who was killed by an Israeli strike in Gaza while she was waiting for aid. The proceeds from the song went to the United Nations Relief and Works Agency for Palestine Refugees in the Near East. He also helped produce a film about the Columbia University Gaza solidarity encampments that premiered in 2025.
Macklemore has also drawn attention to the contrast between his own stance on Gaza and Sheeran’s decision to remain publicly neutral on the conflict. The pair have been friends for 13 years and released a song about fatherhood, “Growing Up,” in 2015, and Macklemore described the “Shape of You” singer as a “brother” in his Instagram statement.
But he has also questioned whether Sheeran’s carefully apolitical public image is still tenable. “There is no neutral position between the oppressor and the oppressed,” he wrote in his statement announcing his departure from Sheeran’s tour. “It’s 2026. Being apolitical during a genocide doesn’t work anymore. People are asking artists to show up, educate themselves and be in community. To use the stage for more than entertainment.”
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In his music, Macklemore has offered songs in support of the Black Lives Matter movement and LGBTQIA+ rights. In 2016, he released the single “White Privilege II,” addressing systemic racism, police violence and his position as a white artist making rap music. In the song, he questioned his own role in profiting from a predominantly Black genre, rapping, “We take all we want from black culture, but will we show up for black lives?” In an interview with Rolling Stone that year, Macklemore said that the topic of his song “might affect sales, this might affect touring, but it doesn’t matter if I’m not speaking up – if I’m not pushing myself to speak truth.”
Whether you’re familiar with any of Macklemore’s discography beyond “Thrift Shop,” his music has only gotten more political since. “Same Love,” written to support Washington state’s Referendum 74 that legalized same-sex marriage, became an unofficial anthem celebrating gay rights. He performed it live at the 2014 Grammy Awards alongside Madonna and Mary Lambert, during which 33 couples were married live on television by Queen Latifah.
The rapper has directly criticized Donald Trump’s presidency in his music, too. He released “Wednesday Morning” about his concerns for the future of the U.S. after waking up to the 2016 election result. “Bad taste, bad taste in my mouth,” he rapped. “Flag wavin’, flag wavin’ at a patriot’s house.”
There have been missteps, too. In 2014, Macklemore faced backlash after appearing onstage in a costume featuring a large prosthetic nose, black wig and bushy beard. Critics accused the rapper of invoking a longstanding antisemitic Jewish stereotype. Macklemore issued an apology on his website at the time, saying, “Family, friends and fans alike who know me well know that I’m absolutely not the person described in certain headlines today. There is no worse feeling than being misunderstood, especially when people are hurt or offended.” He said that he intended to “surprise the people at the show with a random costume” and acknowledged that it could be “ascribed to a Jewish caricature.” At the time, the Anti-Defamation League accepted his apology.
Throughout the media storm that has accompanied Sheeran’s tour, Macklemore has continued to turn attention towards the reality for Palestinian people. “I want to bring the conversation back to where it belongs: to the Palestinian people who are still being killed, still living under military occupation and still fighting for their freedom,” Macklemore wrote on Instagram last week. While urging Kraft to match his $1 million donation, he told the billionaire: “Whatever we disagree about, perhaps we can agree on this: Palestinian lives are worth protecting. A Palestinian life is no less valuable than any other life on this earth.”
For an artist whose biggest hit was built around the thrill of finding something nobody else wanted, there is something fitting about Macklemore’s career taking him somewhere few would have predicted. He has gone from the bargain bins of Goodwill to the front line of one of the most divisive political debates in the world — and shows no sign of stepping back. As he himself put it: “If the words [free Palestine] cost me the stage, while turning the conversation back onto Palestine, then it was the most successful tour I’ve ever been on.”