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.
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.
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 of 2014 Chapel Perilous was selected as a Vimeo Staff Pick.
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.
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.
Lessner directed the music video 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 contributed lyrics to 6 of the 8 tracks on Lydia Ainsworth's debut album Right From Real, which was released on Arbutus Records in 2014. Additionally he directed the music video for Ainsworth's single Malachite, which Stereogum voted video of the week in June 2014. 
Lessner has collaborated with Cameron Stallones of Sun Araw who contributed to the soundtrack for The Woods. In 2009 they released Sun Araw featuring Matthew Lessner - In Orbit through stunned records.
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.
|2005||Darling Darling||Short Film|
|2007||By Modern Measure||Short Film|
|2011||The Woods||Feature Film|
|2013||Chapel Perilous||Short Film|
|(unknown)||Terror Tuesday||Feature Film|
|2009||"Set in Stone"||Fires of Rome||The Hours Records|
|2009||"Set in Stone" M83 Remix||Fires of Rome||The Hours Records|
|2009||"Stillness is the Move"||Dirty Projectors||Domino Records|
|2009||"Surprise Hotel"||Fool's Gold||IAMSOUND Records|
|2009||"Last Dance"||The Raveonettes||Vice Records|
|2009||"Early Warnings"||Foreign Born||Secretly Canadian|
|2010||"Forgive Me"||Le Loup||Hardly Art|
|2010||"World News"||Local Natives||Frenchkiss Records|
|2010||"Neverest"||Hey Champ||Townie Records|
|2012||"Marathon Runner"||Yellow Ostrich||Barsuk Records|
|2014||"Solo Wallet Shuffle"||Sun Araw||Drag City|
|2010||Dirty Projectors + Björk||Mount Wittenberg Orca I, II, III, V VI||Album Trailers|
|2011||Explosions in the Sky||"Last Known Surroundings"||Video Installation|
- Pallone, Cara (July 31, 2008). "RHS Grad to film locally". The News-Review. Retrieved 2009-10-18.
- "Utopia Unplugged". Film Stew. August 1, 2008. Retrieved 2009-10-18.
- Dodge College alumni make Sundance debut
- http://www.imdb.com/title/tt0481503/releaseinfo?ref_=tt_ql_9. Missing or empty
- Everleth, Mike (August 16, 2007). "Darling Darling". Underground Film Journal. Retrieved 2009-10-18.
- "Wolphin No. 6". Wolphin: A DVD Magazine of Unseen Films. Retrieved 2009-10-18.
- http://www.clermont-filmfest.com/index.php?m=213&c=178&n1=c&n2=%20&n3=1023&annee=2014&id_prog=100000182. Missing or empty
- "Film Screening - By Modern Measure". South By Southwest. March 2007. Retrieved 2009-10-18.[dead link]
- http://www.imdb.com/title/tt0939597/releaseinfo?ref_=tt_ql_9. Missing or empty
- "Film Screening - By Modern Measure". Sundance Film Festival. January 2008. Retrieved 2009-10-18.
- "Film Screening - The Woods". Sundance Film Festival. December 2010. Retrieved 2010-12-03.
- Miller, Daniel. "SUNDANCE: How 'The Woods' ' Unique Financing Model Could Shake Up the Festival". The Hollywood Reporter.
- Breihan, Tom (July 16, 2009). "Director's Cut: Dirty Projectors: "Stillness is the Move"". Pitchfork Media. Retrieved 2009-10-18.
- http://stereogum.com/104541/best_music_video_2009/the-gummy-awards/. Missing or empty
- Breihan, Tom (September 24, 2009). "Video Premiere: Fool's Gold: "Surprise Hotel" (New Version)". Pitchfork Media. Retrieved 2009-10-18.
- Monte Lomax Productions
- RODS Films
- Matthew Lessner at the Internet Movie Database
- Collected Music Videos of Matthew Lessner
- The Woods Teaser 1
- The Woods Teaser 2