Today, Tim O’Brien is a renowned, successful artist who paints portraits of some of the most famous and infamous people in our history. Those portraits have graced the covers of magazines like Time, Rolling Stone, Esquire, Newsweek, and more. Some of his work – 13 pieces actually – hang in the National Gallery of Art in Washington, D.C. But in the early 1980s, as a student at North Haven High School, O’Brien was a regular teen struggling with who he wanted to be and where his life was headed.

O’Brien grew up in the Montowese section of North Haven, and even at the elementary school level teachers noticed his extraordinary talent for art. Though art was a natural talent for him, he began to resist it in high school years.

“I was always an artist,” he said. “This was always my thing. For me, I waver between being inspired by art and being crushed by it.”

But he thought for a while that he might want to be a boxer, or a cop. O’Brien remembers telling his guidance counselor that he was thinking of being a cop. “He said, ‘what about being a police artist?’” O’Brien recalled with a laugh.

Reluctantly, he stuck with his art, and began to really apply himself during his senior year.

“Tim was what we considered a child prodigy,” said Ann Cappetta, the high school art department coordinator. “He had so much talent that we called the state art consultants to look at his work, from which we determined that he was way ahead of his years.”

Art teacher Diana Blythe had O’Brien as a student in her in drawing and painting classes, and said his artwork was “superb and unsurpassed...certainly some of the best I have seen in over 25 years of teaching.”

While his teachers certainly noticed his talent, it apparently did not go unnoticed by his peers. Blythe recalled that O’Brien once sold one of his pieces to a classmate for $100.

After graduating in 1983, O’Brien went on to study art at the Paier College of Art in Hamden, where he said he got really great training on how to paint realistically. He got an agent, and one of his first jobs as an artist was to draw book covers. O’Brien eventually moved into the world of portraits, for which he has become most well-known.

“This past year with the really long primary and election season I got really busy,” O’Brien said. “I think I painted Obama 17 times.”

O’Brien was back in North Haven last week as a guest in Blythe’s art classes. The two reconnected several years ago at a class of 1983 reunion, and this is the second time that the artist has presented to her students. O’Brien brought many samples of his work, described his painting process and demonstrated his technique.

“I find that if you just start drawing ideas flow,” O’Brien told students.

His discussion was in preparation for an assignment Blythe’s students are currently undertaking – painting a portrait of someone representing the Civil Rights movement.

“My goal is always to bring as much of the real world into the classroom as I can because that is where the children must ultimately exist and function as members of society,” Blythe said. “Having someone as professionally and personally successful as Tim come to visit shows kids the importance of pursuing dreams with hard work and focus in order to make them a reality.”

O’Brien showed students his portraits, which included slain rappers Notorious B.I.G. and Tupac Shakur, as well as world leaders like former President George W. Bush, former Vice President Al Gore, Sen. John McCain, and former Russian President Vladimir Putin. O’Brien painted Putin’s portrait for the cover of Time when he was chosen as the 2007 Person of the Year. His portrait of Putin didn’t ultimately make the cover of the magazine, but another of his portraits for the title did – one for Bill Clinton and Kenneth Starr, who were the Men of the Year in 1998.

“I often get hired to do something reverential,” O’Brien said. “Or I get hired to make fun of someone, mock them.”

Some of O’Brien’s other work has included the 2000 Earth Day poster, and a portrait of Paul McCartney for last year’s Grammy Award program.

O’Brien lives in Brooklyn with his wife Elizabeth Parisi, and their son Cassius.

For more about Tim O’Brien visit www.obrienillustration.com.