Fielder was interested in comedy from a young age, and as a teenager was involved in his school's improv group, which also featured fellow comedian Seth Rogen. He majored in Business at the University of Victoria, which would later influence his work. After attending a comedy course at Humber College, Fielder started his career as a correspondent for CBC's This Hour Has 22 Minutes for the segment series Nathan on Your Side from 2008 to 2009. Fielder would later write and appear on the American sketch showImportant Things with Demetri Martin (2011).
In 2013, he co-created and directed the Comedy Central parody reality show Nathan for You, in which Fielder stars as a slightly more awkward version of himself, who offers advice to struggling businesses. The show ended in 2017 and was followed by the HBOdocu-comedyThe Rehearsal (2022–present). Fielder also executive produced the HBO docu-series How To with John Wilson (2020–2023). In 2023, he and Benny Safdie created his first scripted show, Showtime's The Curse, in which he stars, alongside Safdie and Emma Stone.
In 2013, Fielder co-created his own show on Comedy Central called Nathan for You.[10] The show, which he wrote, directed, and starred in, was based on the "Nathan On Your Side" segments that he did for This Hour Has 22 Minutes.[10] The show's premise features Fielder, playing a persona loosely based on himself, providing advice for local small businesses.[7][19] In November 2017, the show finished its fourth and final season.[20]
On the morning of February 7, 2014, a coffee shop called Dumb Starbucks Coffee opened in the Los Feliz neighborhood of Los Angeles.[21] The shop stated that they were operating as a parody of the global coffee company and coffeehouse chain Starbucks and utilized the chain's siren logo in their signage, cups, and other materials.[22] In the episode Fielder states that his understanding of parody law is “based off what I read on Wikipedia.”[23] The shop mocked items standard to most Starbucks' locations such as Norah JonesCDs and drinks by using the term "Dumb" in front of the names, such as "Dumb Norah Jones Duets" and "Dumb Iced Vanilla Latte".[22] Beverages and pastries were distributed free of charge.[21] Some journalists initially speculated it was the work of British artist Banksy.[24] A few days later, Starbucks announced that they were not affiliated with the shop and that they were "evaluating [their] next steps" due to the shop deliberately attempting to mimic the look of a legitimate Starbucks location.[25]
The identity of the person behind the shop was not released initially, and various artists and comedians such as Banksy[26] and Tim & Eric were theorized to be involved with the prank[27] (the latter’s production company Abso Lutely Productions had applied for a filming permit at the Dumb Starbucks Coffee location).[28] On February 10, 2014, the shop was closed by the Los Angeles County Health Department for not having the permits required to operate a coffee shop.[29] Shortly thereafter, Fielder announced that he was behind the parody and the Los Angeles Times noted the prank's similarity to other skits performed on Fielder's show Nathan for You.[30]
Fielder started a not-for-profit company called Summit Ice Apparel in 2015, after learning that the Vancouver-based company Taiga posted a tribute to Holocaust denier Doug Collins. He decided to start his own company and produce soft shell jackets. This endeavor was shown during Season 3 of Nathan for You. 100% of Summit Ice Apparel's profits go to the Vancouver Holocaust Education Centre in Vancouver.[31] The company had close to $500,000 in sales in the first three months.[32] In March 2017, he opened up a pop-up shop in Vancouver where members of the public could buy Summit Ice Apparel or exchange their Taiga jacket for a Summit Ice jacket. Fielder himself worked the register. A film crew was also on-site.[33][34]