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In late 2018 Lessner was awarded a grant from the Swedish art council Kulturbryggan for the development of an interactive film exhibition entitled SAINT Y2K.

In 2017 Lessner released his second feature film Automatic at Sea, which became embroiled in the Pizzagate conspiracy theory prior to its release, resulting in Lessner receiving death threats and being accused of creating coded propaganda for the Clinton Foundation. Werner Herzog called the film "unusual and courageous". Automatic at Sea screened at festivals and theaters worldwide including at the Slamdance Film Festival, the ArcLight Hollywood, the American Film Festival, and the New Hampshire Film Festival where the film won the Narrative Grand Jury Prize.

In April 2016, Champis Solutions, a solo installation by Lessner opened at Nevven Gallery in Gothenburg, Sweden. Champis Solutions was Phase Two in the ongoing Seven Phase project titled in Anticipation of the Unexpected.

His third short film, Chapel Perilous featuring Sun Araw was an official selection at the 2014 Sundance Film Festival where it won the Short Film Audience Award. The film premiered internationally at the Stockholm Film Festival. In March 2014 Chapel Perilous was selected as a Vimeo Staff Pick.

Lessner contributed lyrics to 6 of the 8 tracks on Lydia Ainsworth's debut album Right From Real, including "Hologram" which was named Best New Track by Pitchfork (website) The Album was released on Arbutus Records in 2014 and was a shortlist nominee for the Juno Award for the Electronic Album of the Year. Additionally he directed the music video for Ainsworth's single Malachite, which Stereogum voted video of the week in June 2014.

In August 2011, Lessner was awarded a San Francisco Film Society and Kenneth Rainin Foundation Filmmaking Grant for screenwriting in support of feature film tentatively titled Terror Tuesday. In May 2012, Lessner was awarded an additional San Francisco Film Society and Kenneth Rainin Foundation Filmmaking Grant for development of the feature tentatively titled Terror Tuesday.

In 2011 Lessner created and directed the web series "Make a Friend" for the French website Konbini.

Lessner has directed over a dozen music videos including for the Dirty Projectors' single "Stillness is the Move" which was ranked one of the best music videos of 2009 by Stereogum. He also directed the video Fool's Gold's "Surprise Hotel".

Lessner has collaborated with Cameron Stallones of Sun Araw who contributed a cover of Neil Young's 'Thrasher' to the soundtrack for The Woods. In 2009 they released Sun Araw featuring Matthew Lessner – In Orbit through Stunned Records.

Lessner's second short film, By Modern Measure, premiered at South by Southwest and screened at 30 film festivals including the 2008 Sundance Film Festival. In January 2011 the Sundance Institute released "By Modern Measure" on The YouTube Screening room as part of its Sundance Film Festival Classics series.

In August 2008, Lessner began work on his first feature film The Woods, which was filmed in the woods around Lookingglass, Oregon. The Woods was invited to world premiere at the 2011 Sundance Film Festival. The film made history as the first film to premiere at the Sundance Film Festival that used Kickstarter for production financing. The Woods premiered in New York at the BAMcinemaFest held at the Brooklyn Academy of Music. The Woods premiered internationally at the Cologne Conference in Cologne, Germany.

Lessner and his younger sister Sophia Lessner have collaborated on a musical project called Masons . They released their first tape In the Basement of the Temple through Stunned Records in 2008.

In the spring of 2008 Lessner worked as an intern for syndicated news program Democracy Now!

Born in Walnut Creek, California, Lessner was raised in Roseburg, Oregon, where he attended Roseburg High School. He graduated in 2005 from Chapman University, where he studied film.

Lessner's directorial debut was the 2005 short film Darling Darling starring Michael Cera, which screened at over 30 film festivals worldwide including the Clermont-Ferrand International Short Film Festival, Comedia, and the Ann Arbor Film Festival where Lessner won the Tom Berman Most Promising Filmmaker Award. The film is included on the sixth issue of Wholphin DVD magazine with alternate audio versions by John Cleese and Daniel Handler. Darling Darling was included the Clermont-Ferrand International Short Film Festival's Retrospective 2014: the twenty-first century American short films.