Alumnus and Television Club Stalwart Found Great Success as Writer, Director, and Producer in Hollywood

Anthony Caleca ’88SVC knew one thing throughout his life: he enjoyed making people laugh. More importantly, he was good at it. He honed that talent while also learning essential production skills at St. John’s University’s state-of-the-art Television, Film, and Radio Center; parlaying those gifts into a lifelong career that included a 16-year run as one of The Tonight Show’s head writers.

A native of Borough Park, Brooklyn, Mr. Caleca attended Nazareth Regional High School, and his parents were eager for him to attend a local Catholic university. “My father loved the idea of me going to St. John’s. He had heard all these great things about it through friends and coworkers whose kids attended.”

Mr. Caleca’s main concern was that St. John’s featured a program geared toward television and film production. At the time, St. John’s featured a working television studio on the cusp of a significant renovation. “It wasn’t until about sophomore year that I noticed the TV studio,” he recalled. “We had this older facility that was about to be redone. I worked in the older version, and then they switched to state-of-the-art equipment.”

While Mr. Caleca’s first love was writing and performing, he was not sure he would succeed in those endeavors, so he immersed himself in the technical aspects of production, joining the Television Club (now known as WRED-TV), and working both in front of and behind the camera, which provided him with valuable experience.

“I always believed I would get somewhere, but I was also very realistic,” he stressed. “I was a great fan of Saturday Night Live and Second City Television, and knew that’s what I really wanted to do. I wanted to make people laugh more than anything else.”

Mr. Caleca became ubiquitous for celebrity impersonations and comedy sketches, which he contributed to Redmen Magazine, the club’s weekly television program, which then aired within the University and on local public access television. “We didn’t have a lot of bells and whistles or elaborate sets, but we had good content and could make something fun and engaging.”

With the club, “I found something I could look forward to. This group of people had something in common with me. I enjoyed having this group that was interested in everything I was; it was a very accepting and creative group of people, which was important. Having that at St. John’s was wonderful.”

Mr. Caleca became fast friends with Michael Sheehan ’87SVC, a like-minded student who would go on to work at St. John’s and have a successful career in television and film production. “He knew what he was doing. Technically, he was ahead of the game and so creative. I knew I needed to align myself with him. Not only was he fun to hang out with, but I learned so much from him and valued his advice on things.”

Mr. Sheehan spoke glowingly about his 40-year friendship with Mr. Calceca. “In less than one minute, I knew he was the funniest person I ever met,” he recalled. “His creativity is endless, and his imitations are spot on. We could meet someone and by the end of that meeting have an entire comedy routine mapped out. The one thing I can say about Anthony is he is always on, always ready.” Mr. Caleca and Mr. Sheehan are members of the WRED-TV Hall of Fame, with Mr. Caleca’s induction coming in 2013.

One significant opportunity for Mr. Caleca came when an outside producer rented the St. John’s facilities to shoot a series of PBS specials hosted by legendary NBC anchor Edwin Newman. “I did the teleprompter for Edwin’s specials. Now I did something that was going to air outside.”

At the same time, Mr. Caleca began to see his comedy sketches were landing well with students watching Redmen Magazine on campus. “Seeing people enjoy my material, as simplistic as it was, as imitative as it was, really encouraged me.” 

The same producer who brought in Mr. Newman brought Jim Henson and the Muppets to St. John’s and Mr. Caleca worked on that project as well. “That was a fantastic experience. The TV Club afforded all these opportunities you wouldn’t have outside of New York City.”

By junior year, Mr. Caleca had won several awards for video projects he submitted to various student competitions and was able to develop a “clip reel” he could show to prospective employers. He was interviewed for an internship at Fox News and offered a position at the nascent news magazine, A Current Affair, a program that spawned countless imitators over the years. 

“It was the first tabloid-style news show, and they did a lot of fun, lighter pieces that played to my strengths. I would sit in the editing room with producers and make suggestions. They would listen to my ideas. I would go on shoots. I felt like I was doing it longer than I had because I was already doing that stuff at St. John’s. I already had cameras on my shoulder and shooting experience.”

Mr. Caleca’s internship was extended into his senior year, and then he was offered a full-time position as a production assistant. This was December 1987, and he was slated to graduate in May 1988. “I wanted to finish my degree, but I didn’t want to lose the opportunity,” he stressed.

Initially a Computer Science minor, but Mr. Caleca was told he would have to forego the minor (which he switched to Business), but had enough credits to graduate. He graduated in January of 1988 and his career journey began in earnest.

Mr. Caleca quickly moved through the ranks at A Current Affair, becoming a story coordinator, working closely with producers on segments and writing sketches satirizing current events. “I was better with the lighthearted material,” he noted. 

At the same time, Mr. Caleca, encouraged by friends and colleagues, tried his hand at stand-up comedy. During one of his first appearances, he followed Jon Stewart, whose set was very similar to Mr. Caleca’s. Off the cuff, he decided to riff on how Mr. Stewart did half his act before he could, and it went over well. He did stand-up regularly —until fate intervened.

Several of Mr. Caleca’s bosses were hired away from A Current Affair to take over Hard Copy, a competing tabloid show in Los Angeles, CA. The new regime did not appreciate Mr. Caleca’s humor so he hastened change in his fortunes. When his former colleagues visited New York, he made it his mission to show up wherever they were and explain his situation. Before long, he was offered a job at Hard Copy in Los Angeles, which has been his base of operations ever since.

He continued his parody sketches there, which became more expensive and elaborate. By then, he wanted to enter comedy full time. In 1993, he was hired to write and direct sketches for a show called Comicaze at MTV. 

“I met the world of comedians who are now big stars today: Judd Apatow, Ben Stiller, Janeane Garofalo, Bob Odenkirk, David Cross, and many more. It was my first real taste of Hollywood. It was a fantastic opportunity to make connections.”

Mr. Caleca continued his stand-up career and would do freelance writing for shows featuring Jon Stewart and Rosie O’Donnell. In 1997, he was hired as a director on The Kennan Ivory Wayans Show. 

“It was the first diverse show I ever worked on, and I learned so much. Keenan opened up my life, and I got to work with writers with an edgier sense of humor. He was a terrific mentor.”

The show only lasted six months, but the experience was critical, as it was Mr. Caleca’s first break into late-night comedy. He continued freelancing while looking for another full-time position. In June 1998, he received a call that would change the trajectory of his entire career. The head writer of The Tonight Show with Jay Leno was looking for a director with writing experience. After receiving numerous copies of Mr. Caleca’s reel over the years, he finally viewed it.

Eventually, he decided to bring Mr. Caleca in for a 13-week contract. “I did movie parodies and commercial parodies and whatever they threw at me because they saw I did visual stuff well. I wasn’t a monologue writer who supplied Jay’s jokes. We would do ‘drop-ins,’ monologue jokes with a visual connection.” 

Mr. Caleca also filmed segments in the field both locally and nationally, traveling all over the country with comedians doing red carpet work or at major events like the World Series. “You could tell who was on their way to something, and who wasn’t, based on their attitude,” and how well they accepted constructive criticism, he noted.

Mr. Caleca pioneered the type of sketch where a comedian or host would interview real-world individuals. “Jay trusted me because my pieces performed well. I always came back from the field with something. I tell people, ‘Don’t ever say no to anything.’ You can always make something out of nothing and create an angle to get the funny out. I never wasted the show’s resources.”

He added, “I tell interns and students coming up to never give up on your goal for the piece is, or how to get the joke out. It is not impossible to come up with an angle to sell that piece. The Tonight Show taught me to think on my heels.”

Since The Tonight Show ended, Mr. Caleca has worked for several shows, including The Talk and The Kelly Clarkson Show. “I was so good at shooting field bits because of this dream that started at St. John’s when we would just go out and shoot something fun. I was never out of a job.”

A well-known industry name who has won three Emmy® Awards, today Mr. Caleca primarily works as a freelance jack-of-all-trades, who producers and showrunners call to finesse shows with his brand of writing and sensibilities for comedy sketches.

“St. John’s taught me that you could have vision, but you must apply yourself and listen to whoever’s in charge. If you take things too far, it doesn’t help anybody. You have to think of the needs of the production itself and stay within those parameters. I learned editing, timing, and how to make things more concise at St. John’s.”

Mr. Caleca was one of the first writers to work with Sebastian Maniscalco, now a major force in comedy with several successful Netflix specials, and he finds those experiences the most gratifying. 

“One of my strengths was working with regular folks and making them shine, or with young comedians who didn’t know how to work in front of a camera and are now on Saturday Night Live. That is so rewarding.”