Even though he was a regular on five series, the role actor Vincent Ventresca is best known for is Fun Bobby on NBC’s hit sitcom Friends.

For two episodes.

That were a season apart.

And more than 27 years ago at that.

“More people saw those two episodes than anything else I’ve done. It’s a show that just keeps going, finding a new format; it’s being introduced to a whole new generation. That show became its own thing, its own world. It was a funny bit on a show that everybody saw. It’s rerunning all the time,” said Ventresca, 56, who lives in Los Angeles with Dianne, his wife of 27 years, with whom he has two children.

On Friends, Fun Bobby was the love interest of Monica (Courteney Cox), debuting in the Season 1 episode, “The One With the Monkey.” The life of the party, Fun Bobby is known and loved by all. He arrives late to a New Year’s Party, revealing his grandfather died and he wasn’t able to get a flight out, bringing everyone to tears.

“Not a lot of people remember that Friends in its first season was a moderate hit. All of them were relatively unknown with the exception of Courteney (Cox)… They were all happy to have a job,” recalled Ventresca. “At the end of (my episode), producer David Crane said to me, ‘We’ll have Fun Bobby back.’ I was like, ‘Great.’ I’ve been told ‘We’ll have you back’ a lot… Whenever they say that, they’ll never have you back.”

However, Crane kept his word and brought Ventresca back the following season. In the Season 2 episode, “The One With Russ,” Monica gives Fun Bobby another chance. However, it’s revealed he’s an alcoholic. Monica successfully helps him stop drinking. Once he does, he’s no longer fun to be around. In fact, Chandler (Matthew Perry) calls him “Ridiculously Dull Bobby.” Ironically, Monica begins drinking heavily around him, so she can be entertained in his presence. As a result, Fun Bobby thinks she has a drinking problem and breaks up with her.

“We would do a very fast run-through while putting on makeup… I had my wardrobe on. It was a muted color. (Producer Marta Kauffman) or Courteney suggested that I should be wearing something bright because I’m Fun Bobby. I changed into a red turtleneck, so I appear (in the episode) and I’m bright, I’m bouncy, I have all this energy, then I picked up Joey (Matt LeBlanc). It was just a good bit that worked. Who knows how things work on television?” said Ventresca.

Between the first and second seasons, Friends’ popularity skyrocketed. The cast appeared on the cover of Rolling Stone and became very famous. At one point, the cast was making $1 million/episode. For Ventresca, witnessing this was like night and day.

“It was like I’d been to a different planet,” he said. “There were metal detectors, there were helicopters… The set was packed with people all over the place. (The cast) didn’t change; they were still the same. It was exciting and scary. They were huddled together just trying to ride it out. They were an incredible group, and they were lucky to go through it together.”

Ventresca confessed he was intimidated working with them.

“I pretended I wasn’t, but I was,” he said. “They were all such great people. Courteney was so welcoming. She included me in the group. It sorta sucks going on someone else’s show because it’s like they’re having a dinner party – it’s their dinner party – and oftentimes you feel as if you’re sitting at a different table, then you leave. However, Courteney was very deliberate and mindful to include me in the group and all they were doing… She was really cool about it.”

Fun Bobby has become a cult character in his own right. Food, such as the Fun Bobby Hangover Burrito, has been named after him, according to Ventresca.

“I think he was a relatable character for a lot of people,” he said.

Asked what Fun Bobby would be doing now, Ventresca laughed. “Funny you should ask.”

Ventresca isn’t done with Fun Bobby yet. He’s written a spec script where it’s revealed Fun Bobby’s returned to his Midwestern hometown to care for his ailing parents.

“I always thought Fun Bobby should have his own show,” he said. “I know a lot of writers from TV shows who’ve helped me structure it… Fun Bobby has to help his mom and dad – that becomes his new mission in life. He’s Ridiculously Sad Bobby at this point. That’s sorta the bit: He has this mid-life angst, but everyone who sees him lights up because of what he means to them. At some point, maybe that’s enough – to be that person that people loved. He doesn’t feel like his own life was wasted.”

Part of the Family

When he was a senior at Bishop Chatard High School in Indianapolis, the only college Ventresca applied to was Indiana University. Ventresca joked he majored in basketball and partying his first two years at IU.

Around that time, the 1986 basketball movie Hoosiers was being filmed in Indiana. Basketball players were needed as extras, so Ventresca auditioned. Although he didn’t get the part, his was career path was set. At the beginning of his junior year, Ventresca took an Acting I class. At that point, everything pivoted toward acting. He double-majored in theater and psychology.

“It was a good trade-off because as an athlete and a basketball player, becoming an actor is pretty fluid,” he said. “It’s very similar in its preparation. There’s a performance, there’s game-time, there’s equivalence on both sides. I took hold of all those skills and my love of it – when you love something, you don’t mind doing it. It’s so much fun to be rehearsing a play until midnight and coming back the next night to work on it again and get better so you can be ready for opening night. Then performing it over the course of the run.”

Alongside his IU roommate Tuc Watkins (One Life to Live), Ventresca appeared in Eugene O’Neill’s Ah, Wilderness! This was the same night English reggae/pop band UB40 was performing at IU. Before his cue to go onstage, Ventresca was in the green room with UB40.

“We were all in there together,” recalled Ventresca. “There were real rock stars there. There was all this nervous energy. I was just doing this play with a bunch of makeup on my face. It was so weird and so bizarre, then I realized I just joined this group of people who are performers. Like gypsies, I became part of the caravan. It just felt like home – ‘Wow, this is so weird’ – but I loved it. I felt like I found a family I wanted to be a part of… The IU theater department is its own troupe. It was great. It was really helpful because it shrank the school down to size and then you were dealing with the same 150 people all the time and you were going to the same places all the time.”

IU prepared Ventresca well for his acting career.

“There were many talented people there. It’s like basketball – you play as good as who you’re around. I saw the work ethic, how hard it would be to be successful at it. I was surrounded by artists who worked really hard at what they did, and you saw them produce results from their approach,” he said. “The way IU really prepares you is it introduces the approach to acting, the work ethic, and the opportunity to do plays. That’s where the rubber meets the road, whatever that saying is. Getting out there and performing in front of people when the curtain goes up, that’s when you see if this is what you’re built for.”

Small Screen Success

In the early 1990s, Ventresca moved to L.A. He made his TV debut on the legal drama Reasonable Doubt. Next up was The Fresh Prince of Bel-Air, his first foray into sitcoms.

“That was incredible,” he said. “Queen Latifah also guest-starred in the same episode I did. Will Smith was just so generous. He did this prayer before the show.”

From there, he guest-starred on Life Goes On, Blossom, Almost Home, and Diagnosis Murder, before landing his first regular role as Dr. Tom Powell on the short-lived medical drama Medicine Ball, which he called “FOX’s version of ER.”

Then came Friends, which led to his role as Professor Jack Reed on Boston Common. He was the only one who auditioned for the sitcom, which ran for two seasons on NBC from 1996-97. The show was created by David Kohan and Max Mutchnik, who later created Will & Grace.

After Boston Common was canceled due to low ratings, his next major role was Dr. Ed Tate on ABC’s short-lived science-fiction series Prey. His co-star was a pre-Will & Grace Debra Messing. He has fond memories of working with her.

“Debra was awesome – so committed, so smart,” said Ventresca. “She just took the work very seriously – I loved that. We hung out a lot. When you have a friend who becomes really famous, people start calling you on their behalf and inviting you to things. I was cool with that. I’d get invited and there’d be so many people around her, I would have to fight through them to get to her and say hi.”

Admittedly, he didn’t want to do Prey and initially turned it down.

“I don’t remember why. I mean, what an idiot. I was young. You perceive you have power. There’s so much ego you have to navigate with acting. I did pretty well, but there are a couple of jobs I turned down that made no sense. This is embarrassing, but I’ll say it: I became an actor because I wanted to be Al Pacino. At some point, you realize you’re not Al Pacino; you’re Vinnie Ventresca. But there is a moment where you’re still delusional enough to think that you’re someone else that makes you think you should say no to certain jobs. It’s totally ridiculous,” he explained.

Fortunately, ABC offered Ventresca Prey again. They offered him a development deal for another series after Prey ended, sweetening everything.

“My ego loved that – ‘They really want me! They’re gonna let me do another show!’” he recalled. “The whole thing ended up being a mistake with the exception of doing the show. I really fell in love with the show. I really loved Prey. I loved Debra, I loved (creator William Schmidt)… Prey could’ve gone on forever.”

Unfortunately, Prey only aired one season.

“(Schmidt) said, ‘Look, we can’t offer you the part but (then-Warner Bros. Television President) Tony Jonas wants you to have the job, so you’re in pretty good shape, but you have to test for it. Even if you don’t get it, your development deal still holds; we’ll find another job for you.’ I did that. I got the job. I tried to make it my own. I got really interested in it. Your whole job as an actor is to fall in love with the story you’re trying to tell… I threw myself into it,” he said.

However, Schmidt was fired from Prey. Worse, Jonas, who gave Ventresca the development deal, got fired from Warner Bros. And the development deal ended after a year, turning out to be a “very big, fat dead end.”

“That’s what sucks about TV sometimes,” he said.

Kohan and Mutchnik asked Ventresca to contact Messing about Will & Grace.

“There’s a funny story there: Debra didn’t want to do it,” he said. “Prey had not been formally canceled. Debra is a very, very loyal person and she loved that show. Max called me and said, ‘Tell your friend she has to do our show.’ Max sent me the script. I called Debra and said she should do it. ‘But our show’s not canceled yet,’ she said. ‘Debra, our show’s canceled.’ The next day, Prey was canceled. Then Debra called me three days later, telling me she went to (director) James Burrows’ home for a meeting and got the part.”

As for why he didn’t appear on Will & Grace, Ventresca wasn’t funny enough.

“There’s a tone to their humor,” he explained. “They had to push me when I was doing Boston Common. There’s this mode you have to get in for a half-hour comedy. I remember even having problems with Fun Bobby – ‘You’ve got to amp it a little bit.’ I was always trying to be James Dean. I was always trying to be serious. That doesn’t work in a sitcom. Max and Dave probably thought I’m too much work. Plus, they had Eric McCormick. There’s a real fate to these things when they find the right guy. That whole cast – no one could’ve been better for those four parts than the four actors they got. Will & Grace was such a hot show, they could get big movie stars to guest-star. If you could get a movie star to do a guest spot rather than Vinnie Ventresca, that’s probably a good idea.”

Turning Invisible

Ventresca’s favorite role was cat burglar Darien Fawkes, the titular character on 2000-02’s The Invisible Man. This take on the familiar trope was quite different: Facing life imprisonment, Darien is recruited by a top-secret government agency and given invisibility powers via implantation of a special “Quicksilver” gland in his head. However, the Quicksilver gland causes intense pain and antisocial behavior, requiring regular doses of “counteragent” to keep him sane and healthy.

“I really loved that project,” he said. “I thought the script was great. I met creator Matt Greenberg and director Breck Eisner. I knew I was gonna get that part. I was the first person to read for it, too. Matt said after I read for it, ‘It can’t be that easy. That’s the guy we’re gonna hire.’ They saw people for two more months, then they came back to me. That was my part. You kinda know when it’s you.”

The Invisible Man ran for two seasons but was canceled due to budgeting issues and inter-political strife between the Sci-Fi Channel and then-parent company USA Network.

“At least we got to end the show,” said Ventresca. “That was a great group of people to work with.”

Ventresca’s last regular series was ABC’s 2004-05 sitcom Complete Savages. He’s had recurring and guest roles on Dollhouse, Monk, Cold Case, The Twilight Zone, CSI, CSI: Miami, CSI: NY, $h*! My Dad Says (a Kohan/Mutchnik show), Nikita, Psych, Franklin & Bash, Rizzoli & Isles, Wicked City, Nashville, 9-1-1, and Criminal Minds.

Quitting and Persevering

“When I first became an actor, I wanted to prove I could make a living as an actor. I wanted to have a house, a family, and pay for my kids’ school. After I proved to myself I could do that, acting has become a secondary creative thing. Writing is a primary creative thing,” explained Ventresca. “I never really thought about telling stories; actors are just pieces used to tell a story, but I started thinking about telling stories and what stories were interesting to me. I learned how to write. I write a lot and when I can, I audition for anything that will have me. Still, it’s a very hard, very competitive job.”

To date, Ventresca has completed several spec scripts in addition to his Fun Bobby proposal. He stated he’s constantly learning how to be a better actor and writer.

“(Acting teacher) Sanford Meisner used to say, ‘It takes 20 years to learn how to act.’ I’m just beginning to understand acting just now in a way I never did – and it’s super-exciting to have this thing you’ve been approaching your whole life and now you’re getting to a different phase where you’re just figuring it out,” he said. “If I can say anything, the cool part about being an actor is you really do have to develop all parts of your personality because it tests you in many ways.”

Ventresca continued: “It makes you realize whether you can persevere or not. There is something about perseverance that’s honorable. Most of my life, I quit stuff. I’ve always joked I’m a quitter. I kinda quit my way to this career that is ultimately about persevering… If you can ebb and flow with the sticks and stones acting throws at you, sometimes you can find yourself landing where you’re supposed to be. It’s a rough and tumble road, but I think the best work is ahead of me. Even if I’m wrong, to feel that way is powerful.”