Jon Daly '95: Building Character On and Off The Screen

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Jon Daly '95: Building Character On and Off The Screen

When a thin 16-year-old boy with deep dimples stepped onto the stage at the Friday Night Improv in Oakland, the raucous late-night crowd did a double-take. Wasn't he a little young for this? Shouldn't he be at a high school football game – or in bed?

The 20-something performers on stage had asked for audience volunteers to try their wits at improvisational comedy. Jon Daly, a junior at Shady Side Academy, jumped right in, undaunted by his youth and inexperience.

It was 1993, and Daly, a fan of Monty Python and Ghostbusters, didn't miss a comedic beat, playing off the jokes and straight-lines fed to him by the Improv's established performers. The audience howled with laughter at the precocious kid.

Sitting near the stage, Melena Ryzik '94 stared up at her friend and SSA classmate. She knew he was a funny guy, but she was witnessing an amazing seat-of-his-pants comedy performance. "He killed," she recalled.

The audience at the Friday Night Improv saw a teen with natural timing and an imaginative flair for sketch comedy. But they had no way of knowing they were watching the accidental world debut of a future A-list Hollywood comedic actor, writer and producer.

Sixteen years later, Jon Daly is a national name in comedy, acting and collaborating with stars such as Zach Galifianakis, Adam Scott and Ben Stiller. In fact, Daly helped Stiller write Zoolander 2 , and acted in it, too. He also performed alongside Stiller in The Secret Life of Walter Mitty, his first big role in a major studio movie.

Currently, Daly is a regular character on Showtime's original hit series I'm Dying Up Here, which focuses on a group of standup comics vying for stage time and fame in an L.A. comedy club in the early 1970s.

The show takes place decades before Daly's career started, and it's fiction. The competitive characters and story lines mirror many of his own experiences in standup, but the comedy world was much smaller and more cutthroat then.

Daly plays Arnie Brown, a sleazeball comic/booker in Goldie's comedy club who bombs on stage and then undercuts the more talented comedians at every turn. With lamb-chop sideburns and a mustard-yellow polyester shirt over bell bottoms and platform boots, Daly embodies Arnie's total sliminess, both outside and in.

"Arnie's Arnie," he said. "He is a guy who will say anything and is motivated by selfi shness and greed. The writers on the show always give me moments of raw 'Arniness' that are delightful. Every script I read, I am like, 'Oh my God, I get to do this. I get to wear this.'" With I'm Dying Up Here being renewed for a second season, Daly says he's excited about being able to play Arnie in all his hilarious hideousness again.

After years of being a starving artist, it's a joy to be a full-time comic – and to have a regular TV role, write his own sketches and get more movie jobs. "I am really happy right now," he said. "I am super-grateful to be able to do this."

Jon Daly's biography doesn't come close to fitting the stereotype of a standup comedian – someone who cracks jokes or uses laughter to mask a tortured childhood or cover up their inner emotional pain.

Growing up in the North Hills of Pittsburgh, he was the youngest of three boys, the son of a doctor and a psychologist. He said his happy 1990s childhood included learning to play the sax at age 8 and rooting hard for Mario Lemieux and the Pittsburgh Penguins.

In the ninth grade he transferred to Shady Side Academy, where he played hockey. He caught the acting bug after landing the lead in the school play, The Crucible.

Looking back, he quipped that a 15-year-old probably shouldn't play the heavy role of The Crucible's tragic hero and angry adulterer, John Proctor. But he loved that Shady Side gave him lots of opportunities like that, and he ran with them.

He got his first formal taste of comedy when he performed in the one-act play The Adventures of Comic Nemo. It was the senior project directed by his friend Ryzik, who's now a writer for The New York Times. "It was straight-up silly comedy," she remembered. "Jon loved getting laughs from the audience."

Along with learning his first acting lessons at Shady Side, Daly also improved his writing skills – something that would help him later when he would sit in the writers' room at Comedy Central.

It started in Dr. Sarah Eldridge's creative writing class, where students had to free-write a children's story in class. After reviewing her student's papers, Eldridge called Daly into her office and said, "Hey, I think you are really good. I really want to see more of your writing." She offered to mentor him, and he showed her his other work. "She really cared about her students," Daly said.

Along with his forays in high school theater, Daly became a regular audience performer on the Friday Night Improv stage, which met in the basement of the Cathedral of Learning at the University of Pittsburgh.

During one improv sketch, the comics were gathered in a pyramid formation and it was Daly's turn to advance the plot. He did an extemporaneous verbal riff on the then-popular video game Q-bert, where the player used a joystick to change the color of squares on a pyramid. "The audience just died," Ryzik said. "It was like, 'Where did you get that?'"

Those Friday Night Improv shows offered more than just good training for his future in standup. Afterwards, Daly and the older improv performers would hang out at Eat 'n Park. "I would get my Smiley cookie with guys who were 28," he said. "It was 2 a.m., and I found it very dangerous and cool and very validating."

He had found his tribe.

After graduating from Shady Side, Daly went to the University of North Carolina School of the Arts in Winston- Salem to study acting. Then he moved to New York, still thinking he would be a serious actor.

But the early joys of stand-up comedy kept a strong hold on him. "Comedy seemed like a viable thing to do," he said, "and I was going for it."

Daly became a regular at the Upright Citizens Brigade, an experimental improv troupe started by Amy Poehler and other comics. He established himself as a talent, but it wasn't easy paying his bills in the Big Apple. He waited tables and took oddball acting jobs.

In 2013, Daly moved to Los Angeles to be closer to the TV and film industries. It was a smart career move. He landed guest appearances on many popular TV shows, such as Parks and Recreation, Brooklyn Nine-Nine, Life in Pieces, Family Guy, New Girl and many more.

People started to notice. "Jon Daly is everywhere," wrote Alex

Russell on the pop culture website Poor Scholars in 2013. "If you're watching something funny in the next few years, you stand a good chance of running into him."

While Jon Daly was working hard to make his name as an outrageously funny comic, another much more famous John Daly was making his name as an outrageously hard-drinking, hard-gambling pro golfer.

Daly got a zany idea on how to capitalize on his famousexcept-for-one-letter name. In 2013 he invented " e Jo(h)n Daly Project" and created a website called, where he photoshopped his own face into the golfer's plaidpanted body.

"The Jo(h)n Daly Project" didn't make Shady Side's Jon Daly famous on Google or anywhere else. But in 2016 the same idea led to him and comedian Adam Scott collaborating on an online spoof of televised professional golf tournaments, The Adult Swim Golf Classic.

In a mock charity match from the Trump National Golf Club in Los Angeles that he wrote and produced, Daly portrayed golfer John Daly while Scott played Scottish pro golfer Adam Scott. (Both comedians were awful golfers. Daly lost to Scott by only one stroke, finishing 72 over par for nine holes.)

Over the years, Daly's fertile mind has hatched many characters – including Sappity Tappity, a drunk English rollerblading Christmas tree, for the comedy website Funny or Die. "It was ludicrous and hilarious," his friend Ryzik said, "but it was a real character that said things that were emotionally true."

After he began writing his own sketches and making videos with fellow comic John Kroll, and in 2013 their work morphed into Kroll Show, a sketch series on Comedy Central. Daly was a writer and a regular performer, playing one of a pair of obnoxious rich guys as well as other characters.

He also got to show off his "yinzer" roots with a sketch called "Pawnsylvania," where he played a pawn shop owner with a thick-as-pierogis Pittsburgh accent while another comic hawked stuff in a Philly accent.

"He was such a gifted improviser," said John Levenstein, Daly's comedy mentor and head writer of Kroll Show. "There area lot of trained improvisers at Second City and Upright Citizens Brigade and you recognize patterns that are not that original. In the case of Jon, he was always very surprising. He separated himself from the pack with his spontaneity."

As a sketch comedy writer and actor on Kroll Show, "you would never know what he would do next," Levenstein said. "He could make the most normal people seem crazy. Not everyone can play a character who is fl at and make them entertaining. Peter Sellers can do it. Jon can do it."

Daly's slate of online videos eventually became his ticket to the big screen. They caught the attention of Ben Stiller, who asked him to audition for his 2013 movie The Secret Life of Walter Mitty. Daly played the part of a neurotic office worker, appearing in his first major studio film and working alongside one of his comedy heroes.

That acting job led to even more collaboration, helping Stiller write Zoolander 2 and playing the role of Agent Filippo. "It was beyond cool," Daly said. "He gave me creative freedom."

An upcoming movie role will allow Daly to channel a childhood comedic hero, Bill Murray. He is playing the role of Murray in an upcoming Netflix movie called A Futile and Stupid Gesture. He studied clips of the famed comedian, getting the Chicago accent and mannerisms, and it's a good bet he'll look a lot like the young Bill Murray when the shooting starts.

Daly's looks are wildly variable from role to role. Perhaps it's because he can scrunch his dimpled face into an expression that can be either goofy or brooding. In fact, he's such a chameleon that people sometimes stop him on the streets of Los Angeles and do a double-take. They recognize him – or do they?

Ryzik has stayed close with Daly, even though they live on opposite coasts. "He is a steadfast friend, welcoming even as his life changed," she said.

"A lot of comedy people do bits in their off time," she said. "But Jon can always be depended on to listen if I need him to listen, without having to deliver a laugh line. That's not to say that he is not hilarious. He spoke at my wedding and brought the house down."

Daly's generous spirit is also evident on his trips home to visit his family. Ryzik said what's great about Jon is that when he comes to Pittsburgh, he's still likely to go out and do an improv show. When he does, she said, "he's treated like a visiting conquering hero, which he is."

For Ryzik, it has been a fun ride watching Daly evolve from intrepid teenage performer to an established and brilliant comedian. "To see him make those very first jokes on stage back then, and now see him play and write all these amazing characters – it's just the best."

by Cristina Rouvalis | Photography provided by Jon Daly
Published in the Winter 2017-2018 issue of Shady Side Academy Magazine