O'Brien was the second of three sons in his family.[3] O'Brien began training as a boxer in high school, going on to box as amiddleweight amateur in thePolice Athletic League.[3][4] At age 18, O'Brien gave up boxing. That same year he received aPell Grant which he used to enroll in thePaier College of Art inNew Haven, Connecticut.[3] He graduated in 1987 with aBachelor of Fine Arts degree. His instructors at Paier includedLeonard Everett Fisher,Ken Davies and Robert Zappalorti.[citation needed] While attending Paier, O'Brien paintedtrompe-l'œil images, which his instructors Davies and Zappalorti were also known to do, in which the viewer of the paintings are deceived into thinking they were seeing an actual object. In one such case, students attempted to use electrical outlets that O'Brien had painted on the wall.[3][5]
Before graduating from Paier in 1987, O'Brien entered into what became a long relationship with his representative Peter Lott. Lott had seen O'Brien's work at theSociety of Illustrators Student Show.[3]
O'Brien credits his first big break as aTime magazine cover done in 1989,[2] painting a small teardrop overlaid on aGilbert Stuart portrait ofGeorge Washington.[8][2] O'Brien was called on again in 2008 to paint another teardrop on the cover ofTime, for the cover story "The Price Of Greed" following the onset ofa global financial recession.[9]
In 1996, O'Brien designed the cover for book#2 The Visitor inK.A. Applegate'sAnimorphs series.
Between 2008 and 2010, O'Brien was commissioned byScholastic Publishing to illustrate each cover ofThe Hunger Games trilogy bySuzanne Collins, including theHunger Games "mockingjay" logo. The images were then used again for promotional posters when the film distributorLionsgate turned the books into a film franchise.[10]
O'Brien closely collaborated on the designs with his wife, Elizabeth Parisi, creative director for Scholastic.[11]
Tim O'Brien has illustrated more covers than any other artist for the last 30 years.[12] O'Brien'sTime magazine covers are in theNational Portrait Gallery of theSmithsonian Institution.[13] Starting in 1989, O'Brien worked withart director Arthur Hochstein, and created over a dozen covers forTime with him.[14]
O'Brien's "The End of Bin Laden" cover, which the artist created in 2002 when editors atTime believed theal-Qaeda leader was trapped and was or would soon be dead in Afghanistan,[5] was not published until nine years later in the May 20, 2011, issue.[2][15] O'Brien used a similar approach for an earlierTime cover, "The Death of Abu Mousab al-Zarqawi",[16] for the June 19, 2006, issue of the magazine.[17] As of 2020[update], O'Brien has had over 30Time covers published, including:
In 2012, O'Brien said the work he was most proud of was his 2008 cover illustration forRolling Stone in which the magazine endorsed candidateBarack Obama for president.[11] The cover, which depicted the future president with a halo-like glow around him, created a mild controversy, with critics of the image saying itdeified the candidate.[30]
For the December 2012 release,Mother Jones printed double covers, in which one cover was sent tosubscribers of the magazine and the alternate cover was shown onnewsstands. O'Brien illustrated both covers in different styles.[36] For the cover that went to newsstands, titledSugar Kills, O'Brien created a surreal vignette of a glass pitcher as a human skull. For the version delivered to subscribers, titledSolitary in Iran, O'Brien painted a lonely jail cell with a single occupant.[36]
Chosen byIrish American Magazine as one of their 100 top Irish Americans, 1999 and 2000[57]
Awards from Society of Illustrators in New York and Los Angeles:Graphis Inc.;Print Magazine;Communication Arts Magazine; the Society of Publication Designers; American Illustration; Art Director's Club
In 2019, Tim O'Brien was awarded all three top illustration awards; bronze, silver and gold, for covers of Donald Trump forTime.[58][59][60]
O'Brien lectures frequently across the country. His speaking engagements have included the Norman Rockwell Museum, the Society of Illustrators, Syracuse University, School of Visual Arts, Pratt Institute, Rhode Island School of Design, andCalifornia College of the Arts.[61]
Up until 2004, O'Brien stayed active in the boxing world of his youth as a trainer.[4] Since 2006, O'Brien has run theNew York City Marathon, raising money for the Children'sIBD Center atMount Sinai Hospital.[63]