Between 1988 and 1992, he studied film, design and animation at the California Institute of the Arts. He is also a self-taught still photographer.
He has been associated with Duck Studios since early 2005. He has been signed to production companies Acme Filmworks (ca. 1992–ca. 1994), Duck Soup Studios (1994–1995) and its division The Front (1995–1997), MJZ and its satellite Stimmung (1997–ca. 1999), and to Windmill Lane and its subsidiary Pusher (2003–ca. 2005).
In 2006, he was asked explore animation concepts for a feature film adaptation of The Amazing Adventures of Kavalier & Clay. The project fell through, but Caliri posted two and a half minutes of concept footage he directed, titled The Escapist v.s. The Iron Gauntlet, on his Vimeo channel.
In addition to this, he also DPed a number of short films, music videos and commercials and taught experimental animation at CalArts.
His brother is drummer Mario Calire.
- Soul Coughing, "Super Bon Bon", released December 1996
- Morphine, "Early to Bed", March 1997, nominated for a Grammy Award for Best Short Form Music Video in 1998
- Cypress Hill, "Boom Biddy Bye Bye (Fugees Remix)", August 1996, co-directed by Dante Ariola
- Marcy Playground, "Sex and Candy", October 1997
- Eels, "Your Lucky Day in Hell", December 1997
- Morcheeba, "Trigger Hippie", 1997, alternate version
- Black Lab, "Time Ago", May 1998
- Cherry Poppin' Daddies, "Brown Derby Jump", July 1998
- Marcy Playground, "Comin' Up from Behind", March 1999
- The Shins, "The Rifle's Spiral", April 2012, co-directed by Alexander Juhasz
- Big Apple, 2001, opening credits
- Lemony Snicket's A Series of Unfortunate Events, 2004, end titles
- Madagascar: Escape 2 Africa, 2008, end titles
- United States of Tara, 2009, opening credits, won the Primetime Emmy Award for Outstanding Main Title Design in 2009
- The Escapist v.s. The Iron Gauntlet, 2006
- The Sun and the Seed, 2008
- Cypress Hill, Cypress Hill III: Temples of Boom, 1995, photography
- Marcy Playground, Shapeshifter, 1999, photography
- The Wallflowers, Red Letter Days, 2002, art direction / packaging / photography
- "Dragon" premiered during Super Bowl XL.
- "Complete List of Academy Voter Picks". Los Angeles Times. Tribune Company. January 7, 1998. p. 15. Retrieved 2014-02-10.
- "Cherry Poppin' Daddies Talk About Getting Surreal In New Video". MTV. 1998-08-03.
- "Media". Marcyplayground.com. Retrieved 2014-02-10.
- "Jamie Caliri – The Sun and the Seed on No Fat Clips!!!". Retrieved 2014-02-10.