Schenectady County

Old friendship rekindled on Jimmy Fallon show

Dion Flynn, 43, whose first appearance on "Late Night with Jimmy Fallon" came last May, is perhaps b

Categories: Life & Arts

The bit’s setup was simple: Host Jimmy Fallon introduced an up-and-coming singer-songwriter, chatted with him briefly and then had him play a couple songs.

Playing the “singer” was Dion Flynn, a performer with 19 other appearances on “Late Night with Jimmy Fallon” since last spring.

Flynn, a former Schenectady County Community College and University at Albany drama student, soon revealed his character wasn’t much of a songwriter. His songs were all about listening to other people’s songs, specifically the late ’90s pop rock group Smash Mouth.

The less obvious theme, perhaps intentionally, was about Flynn and connections to his own life.

There was the music, which is what he came to Schenectady County Community College in the mid-’90s to study. But he switched his focus to drama, with the encouragement of one of his professors.

There was rapport with Fallon. The two became friends when Flynn attended UAlbany and Fallon the College of Saint Rose. That friendship shone through in the mock argument between the “performer” and Fallon, which ended as the two joined in an unconventional Smash Mouth duet.

There was even the name of the character, “Johnny Miles Biter.” Hidden in the name was the name of Flynn’s newborn son, Miles. Flynn credited Fallon with adding the middle name, after Fallon presented Flynn with a “Late Night” onesie for the baby.

“That’s just the kind of stuff Jimmy always does,” Flynn said recently. “He’s just so nurturing. It’s nerve-wracking for me to be trying all this stuff on such a large platform, but the guy is a true friend and a true benefactor in my career, and I give him all the props.”

Flynn, 43, whose first appearance on Fallon’s show came last May, is perhaps best known by Late Night watchers for his portrayal of President Obama, riffing with Fallon in bits where Fallon played Obama’s rival, Mitt Romney.

Flynn’s path to the Fallon show was a long one, which changed course as Flynn attended SCCC.

It also came after he worked through his own personal issues, including growing up not knowing his biological father. Flynn put those issues at the forefront in 2009, when he and some filmmaker friends went out in search of his father, creating a documentary called “Real Father.”

And now Flynn is a father.

Flynn was born in Detroit, grew up in Maryland, ran away to California at age 17, then later joined the Army. After being stationed at Fort Drum, he made his way to Schenectady with the intention of studying music, his then-girlfriend being from the Albany area.

He entered SCCC in the spring of 1993. By spring 1994, he was a drama major. By the end of 1994, he was continuing his studies at UAlbany.

“It was in Schenectady that I realized that you could get greater reward in your artistic work by submitting to technique and submitting to the rigors and discipline of the theater,” Flynn said.

Helping him do that was his drama professor, Sandy Boynton. Her encouragement led Flynn to switch to drama.

“I just pointed out to him, and he saw it in his own work, that he had some talent,” Boynton said last week. “He also had a passion, and it was a passion to perform.”

Boynton recalled Flynn always carried a guitar and, having been in the Army, he was one of the older students in the class.

She recalled him taking projects to unusual places, like winning approval to put on a small performance for inmates at a state prison.

“That’s what Dion was like. He made really good choices and then moved them in a way that students ordinarily would not go,” Boynton said.

Flynn lamented the downsizing of the SCCC drama program. Declining enrollment led to the degree program being deactivated, though the college’s Academic Senate approved a proposal Friday for a new drama concentration: a Humanities and Social Sciences Associates in Arts degree. The proposal is to now be sent to the central administration of the State University of New York for its approval.

While at UAlbany, Flynn won a spot on the short-lived local TV sketch show “Metroland’s Loose Camera.” One of the other performers on the show was a kid from the College of Saint Rose: James Fallon.

Clips from the show are available on YouTube. One, billed as Fallon’s first TV appearance, includes Flynn as an animated police officer at what appears to be a checkpoint. The two characters in a stopped car, Fallon and another performer, impersonate Lenny and Squiggy, the obnoxious upstairs neighbors from the classic 1970s TV show “Laverne and Shirley.”

Years later, the two were back together on Fallon’s show: Flynn as Obama, with the president’s mannerisms down pat, and Fallon as Romney. One skit has the two in a post-debate “hang session,” another Romney’s concession call.

From their time on the Albany show, Fallon and Flynn became good friends. Flynn remembered taking a stack of books out to a creek one day, each taking sentences and weaving together “some sort of weird dadaist story.”

Flynn said Fallon “was the only one back then that had that insatiable appetite for that madcap creativity that I had, that sort of jazz-like riffing.”

From Albany, though, the two went their separate ways, Fallon to California, Flynn to New York City and New York University.

Aside from one chance run-in in New York City, the two didn’t see each other again until 2011, when a friend of Flynn’s from NYU, Josh Radnor of “How I Met Your Mother,” was going on Fallon’s show to promote a movie. He took Flynn along, and his old friend remembered him well.

By then, Fallon had parlayed a stint on “Saturday Night Live” into his own late night talk show.

Flynn had taken the quieter route, ending up as a life coach in New York City, but he didn’t leave the business entirely. In 2006, he won a brief stint on “The Big Gay Sketch Show” on the Logo cable channel. He also got into improv in New York, joining The People’s Improv Theater as a teacher and performer.

Flynn has also done work in recent years locally with the Mop & Bucket Co. improv group, based at Proctors.

In 2009, he explored his own history in a documentary produced with some filmmaker friends.

Flynn never met his biological father. He was raised in Maryland by his mother, who died in 2005, and his adoptive father. In the film, Flynn sets out with only some addresses and a few scraps of information on a quest to find his real father.

In a way, Flynn’s history mirrors that of one of his characters on the Fallon show, President Obama. Flynn’s mother was white, his father black. The film explores the issues in growing up bi-racial. Flynn recalled learning his sense of humor and how to entertain as a sort of defense mechanism, growing up in an all-white trailer park.

The quest to find his real father became one of learning about letting go and being able to move on. Flynn has submitted the film to festivals, without success so far. It was shown, though, earlier this month at the improv theater where Flynn performs. The occasion was the birth of Flynn’s son, Miles. Flynn’s wife, Amy, had Miles Jan. 12.

Flynn said doing the documentary that trying to find his own father prepared him for the life he has now.

“It cleared up mental space,” Flynn said. “When I had unasked questions, I was not able to have the mental space to allow in a wife and a son. I had too many demons I was wrestling with.”

Back to 2011, when Flynn’s friend Radnor brought him along to Fallon’s show, Flynn recalled Fallon recognizing him instantly and making an instant fuss. Afterward, a producer wanted Flynn’s information; Fallon wanted to stay in contact. By May 2012, Flynn was doing characters on the show.

Flynn’s old professor at SCCC, Boynton, has kept in touch over the years, especially now through Facebook. Asked what she thought of her former student appearing on national television, Boynton said she wished she could be more articulate.

“My real reaction,” she said, “was, ‘Yup. That’s where he belongs.’ ”

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