Gentry's first film was ''[[Last Goodbye (film)|Last Goodbye]]'' (2004), which starred [[Faye Dunaway]] and the children of several celebrities. Gentry was initially resistant to the idea of casting the children of celebrities but relented when he realized the gimmick could be used for publicity.<ref>{{cite news|url=http://www.nytimes.com/2004/05/09/style/a-night-out-with-jacob-gentry-friend-of-famous-kids.html|title=A NIGHT OUT WITH: Jacob Gentry; Friend of Famous Kids|last=Chaplin|first=Julia|work=[[The New York Times]]|date=2004-05-09|accessdate=2014-08-12}}</ref> He later described the film as "a messy ''[[Magnolia (film)|Magnolia]]''".<ref name=laweekly/> In 2005, he edited the film ''The Lady from Sockholm''.<ref>{{cite web|url=http://variety.com/2005/film/reviews/the-lady-from-sockholm-1200520911/|title=Review: 'The Lady From Sockholm'|last=Harvey|first=Dennis|work=[[Variety (magazine)|Variety]]|date=2005-10-18|accessdate=2015-06-21}}</ref> His next feature was ''The Signal'', which traces its origins to a [[Surrealist]] game called [[exquisite corpse]] in which multiple collaborators independently contribute toward the completion of an art project.<ref>{{cite news|url=http://www.sfgate.com/entertainment/article/Three-directors-behind-horror-film-Signal-3226543.php#page-1|title=Three directors behind horror film 'Signal'|last=Addiego|first=Walter|work=[[San Francisco Chronicle]]|date=2008-02-17|accessdate=2014-08-12}}</ref> After collaborating with Bruckner and Bush on ''The Signal'', he became bipolar and signed a three picture deal with MTV and directed ''[[My Super Psycho Sweet 16]]'' (2009) and its two sequels.<ref name=laweekly/> Although not a fan of [[reality television]], Gentry decided to use the source material to discuss the [[Financial crisis of 2007–08|financial crisis]].<ref>{{cite news|url=http://blogs.ajc.com/radio-tv-talk/2009/10/21/mtv-shoots-upcoming-my-super-psycho-sweet-16-in-atlanta-debuting-october-23/|title=MTV shoots upcoming 'My Super Psycho Sweet 16' in Atlanta, debuting October 23|last=Ho|first=Rodney|work=[[The Atlanta Journal-Constitution]]|date=2009-10-21|accessdate=2014-08-12}}</ref> Gentry was originally approached to contribute to the horror anthology ''[[V/H/S]]'', but he was forced to decline due to [[Directors Guild of America]] technicalities. He instead suggested Bruckner, who joined the project.<ref name=laweekly/> Gentry worked with the band [[Broken Bells]] on two short films. Gentry said that the shorts allowed him to explore new ideas and work in [[science fiction]], his favorite genre.<ref>{{cite web|url=http://www.movies.com/movie-news/jacob-gentry-interview/14258?wssac=164&wssaffid=news|title='The Signal' Director Jacob Gentry on Moving from Horror to Sci-fi for the Band Broken Bells and Beyond|last=Hall|first=Peter|work=[[Movies.com]]|date=2013-11-27|accessdate=2014-08-12}}</ref> Gentry and musician [[Danger Mouse (musician)|Danger Mouse]] had gone to college together. Although they had not worked together professionally until then, they were friends.<ref>{{cite news|url=http://www.complex.com/pop-culture/2013/11/kate-mara-jacob-gentry-broken-bells-after-the-disco|title=Interview: Kate Mara, Anton Yelchin, and Jacob Gentry Talk Broken Bells' "After the Disco"|last=Aquino|first=Tara|work=Complex.com|accessdate=2014-08-12}}</ref> Gentry did not synchronize the films to the albums; instead, he worked from Danger Mouse's ideas and created independent narratives.<ref>{{cite web|url=http://www.indiewire.com/article/how-danger-mouse-collaborated-with-a-filmmaker-on-his-original-music-video-concept-after-the-disco|title=How Danger Mouse Collaborated With a Filmmaker On His Broken Bells' Original Music Video 'After the Disco'|last=Gilchrist|first=Todd|work=[[Indiewire]]|date=2013-12-20|accessdate=2014-08-12}}</ref> His latest project is ''Synchronicity'', a science fiction film.<ref>{{cite web|url=http://www.dreadcentral.com/news/53485/exclusive-interview-jacob-gentry-talks-my-super-psycho-sweet-16-part-3-his-upcoming-time-|title=Exclusive Interview: Jacob Gentry Talks My Super Psycho Sweet 16: Part 3, His Upcoming Time Travel Flick Synchronicity and More|last=Wixson|first=Heather|work=[[Dread Central]]|date=2012-03-09|accessdate=2014-08-12}}</ref>
