2009–2017: Career with Ryan Lewis
In 2009, Macklemore and Ryan Lewis formalized the collaboration as a duo Macklemore & Ryan Lewis. They released the EP The VS. EP. They also released "Irish Celebration" in December 2009 in anticipation of the release of The Vs. EP. In March 2010, the duo released "Stay At Home Dad", a track that "didn't quite make" Vs. In October 2010, they created the VS. Redux EP. Macklemore used his experience with substance abuse to create the mixtape's song "Otherside", which samples the Red Hot Chili Peppers song of the same title. 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. "Wings" was released on January 21, 2011, followed by "Can't Hold Us" featuring Ray Dalton on August 16, 2011. 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. That same year, the rapper appeared at many U.S. music festivals, including Bumbershoot, Outside Lands, Lollapalooza, Rock the Bells, Soundset, Sasquatch, and Bonnaroo.
Their album The Heist was released in October 2012 and debuted on the U.S. Billboard 200 at number 2 of the week dated October 27, 2012, selling over 78,000 copies. "Same Love" was released on July 18, 2012, and after "White Walls". In January 2013, Music Choice featured Macklemore in the brand new series "Primed", which focuses on emerging artists. In May 2013, Haggerty was featured on Clinton Sparks's single "Gold Rush", along with 2 Chainz and D.A. The Heist World Tour began in August 2012 to promote The Heist.
In May 2014, Macklemore was accused of antisemitism after wearing a costume resembling a common Jewish caricature during a private concert in Seattle, Washington. The rapper released an apology and stated his intention was to disguise himself, not to impersonate any 'type' of person.
In January 2015, Macklemore announced via Twitter that his third studio album would be released sometime in the second half of that year. Despite this, the album was not released until February 26, 2016. On August 5, 2015, Macklemore released a song for free download titled "Growing Up (Sloane's Song)", which features Ed Sheeran. On August 27, 2015, he released a new song called "Downtown" which features Foxy Shazam vocalist Eric Nally, Kool Moe Dee, Melle Mel, and Grandmaster Caz, which he performed at the 2015 MTV Video Music Awards on August 30. On his first tour in two years, An Evening with Macklemore and Ryan Lewis, Macklemore announced that his new album was finished and ready for release.
On January 15, 2016, Macklemore released a teaser video on his YouTube channel revealing the name of his third studio album, This Unruly Mess I've Made, and announcing that it was scheduled to be released on February 26, 2016. On January 22, 2016, the duo released "White Privilege II", the second single on This Unruly Mess I've Made. On February 26, 2016, Macklemore and Ryan Lewis released the album This Unruly Mess I've Made. Also in 2016, Macklemore released two solo singles, "Drug Dealer" and "Wednesday Morning". "Drug Dealer" features Macklemore rapping about his previous addictions and is featured in a documentary that includes clips of Macklemore discussing drug abuse with President Barack Obama. "Wednesday Morning" was released after the 2016 U.S. Election and features Macklemore rapping about the political future of the country. The tracks were produced by Budo. On June 15, 2017, Macklemore announced via his official Instagram that the duo were on hiatus.
