A native of Seattle, Washington, he started his career in 2000 as an independent artist releasing: Open Your Eyes (2000), The Language of My World (2005), and The Unplanned Mixtape (2009).

[13][14] At the time he started to sing, Haggerty listened to "a lot of East Coast underground hip hop", listing Hieroglyphics, Freestyle Fellowship, Aceyalone, Living Legends, Wu-Tang Clan, Mobb Deep, Nas, and Talib Kweli as his major influences.

[19] Haggerty enrolled at the College of Santa Fe for a year, later saying in an interview that "[i]t was a very pivotal time in a lot of ways.

[17][21] In 2000, Haggerty recorded a mixtape titled Open Your Eyes under the name Professor Macklemore, which he distributed himself and released on October 21, 2000.

[22] Haggerty dropped "Professor" from his name and began working on his first official full-length album, called The Language of My World.

[15] In the meantime, Macklemore kept busy as a solo artist, appearing on The Physics's song "Good" in 2009,[24] as well as performing at the Seattle major arts and music festival Bumbershoot in 2006, 2009, and 2011.

[28] In March 2010, the duo released "Stay At Home Dad", a track that didn't quite make Vs.[29] In October 2010, they created the VS. Redux EP.

[30][31][32] On April 8, 2011, Macklemore and Ryan Lewis performed the song at the 2011 Mariners Opening Day in-front of a sold-out crowd of nearly 48,000 attendees.

In February 2011, Macklemore and producer Ryan Lewis kicked off a multi-city tour in Seattle, which included three sold-out shows at the Showbox at the Market music venue.

[36] That same year, the rapper appeared at many U.S. music festivals, including Bumbershoot, Outside Lands, Lollapalooza, Rock the Bells, Soundset, Sasquatch, and Bonnaroo.

In January 2013, Music Choice featured Macklemore in the brand new series "Primed", which focuses on emerging artists.

[38] In May 2014, Macklemore was accused of antisemitism after wearing a costume resembling a common Jewish caricature during a private concert in Seattle, Washington.

[50] Macklemore stated that it was one of his best performances due to the circumstances and thanked the fans in Sydney for the reception that he received throughout.

[citation needed] On October 29, 2021, Macklemore released a new single titled "Next Year", featuring American singer Windser.

[65] In 2017, Macklemore's grandmother, Helen Schott, celebrated her 100th birthday, with the two traveling around Modesto, California for the music video of his song Glorious.

[69] He said in a 2012 documentary that he spent most of his twenties trying to combat his addictions and destructive way of life: I want to be someone who is respected and not just in terms of my music.

[23]On May 14, 2016, Macklemore appeared in U.S. President Barack Obama's weekly address to talk about the dangers of addiction to opioids and prescription painkillers.

[70] Macklemore talked about his own experiences with abuse of painkillers, stating "When you're going through it, it's hard to imagine anything being worse than addiction.

[73] Recovery Fest was formed to have a drug- and alcohol-free concert and support charities that worked in combating opioid addiction.

[74] In the summer of 2020, during and in part due to the social isolation that took place during the COVID-19 lockdowns, Macklemore relapsed and suffered a near-fatal overdose.

This experience, as well as the ongoing challenge of overcoming addiction while also raising children, served as an inspiration for much of the lyrical content that makes up his third solo studio album, Ben.

[75][76] Macklemore voiced his support of LGBT rights and same-sex marriage in the song "Same Love" released in 2012, which also condemns homophobia in mainstream hip-hop, society, and mass media.

[84] On October 30, 2023, during the Israel–Hamas war, he signed an open letter calling for a ceasefire and an end to Israel's blockade of the Gaza Strip.

[85] In November 2023, while giving a speech at a pro-Palestinian rally in Washington, D.C., he accused Israel of committing genocide against Palestinians.

[88] In August 2024, Macklemore cancelled his show scheduled to take place in October that year in Dubai, citing the United Arab Emirates' involvement "in the ongoing genocide and humanitarian crisis" in Sudan.

[89] At a pro-Palestinian rally in September 2024, Macklemore exclaimed "fuck America", causing widespread controversy, including being dropped from the Neon City Festival in Las Vegas.

[94][95][96] In August 2019, Macklemore joined the ownership group of Seattle Sounders FC, the local Major League Soccer club.