On this episode of We Tawk Funny, Sharon Pfeiffer and Joe Rubo sit down with longtime South Florida talent agent Dona Kay Waterman for an unforgettable trip through decades of entertainment history.Donna has been working as a talent agent since 1990, representing actors, singers, comedians, and other performers across film, television, commercials, and print. But her career in entertainment started long before she became an agent.As a teenager, Donna became an entertainment writer with one major goal: meeting The Beatles. She accomplished it just one year later, becoming the youngest person at an Atlanta press conference and even finding herself face-to-face with John Lennon after tripping over television cables.And that's only the beginning.Donna shares incredible stories from her years interviewing and working around some of entertainment's biggest names, including Bobby Darin, Robert Kennedy, Connie Francis, Sandra Dee and more. She reveals her favorite celebrity encounter, one of her worst interviews, and what it was like navigating the entertainment business before eventually becoming one of South Florida's well-known talent agents.Sharon and Donna also look back at their own history together, including Sharon's acting career, her experience filming Bad Boys, and the unpredictable reality of casting—where sometimes the person who looks nothing like the original description ends up being exactly who gets the role.The stories continue with Sharon and Donna's appearance in the Jonas Brothers' “Cool” music video, which later led to controversy when footage featuring them appeared in an international Coca-Cola commercial.Then Donna takes us behind the scenes of one of her wildest adventures: becoming a two-time contestant search winner for The Price Is Right. From her infamous money pants to doing scissor kicks, winning Jimmy Choo prizes and literally ripping off her wig on television, Donna explains how she became one of the show's most unforgettable contestants.It's an episode packed with celebrity encounters, Hollywood stories, casting secrets, hilarious memories and the kind of uncensored conversation you can only get on We Tawk Funny.Subscribe to We Tawk Funny and join Sharon Pfeiffer and Joe Rubo every week for conversations about entertainment, celebrity, comedy, culture and everything in between.

Eddie Brill spent 17 years working with David Letterman—and the stories he collected along the way are incredible.

On this episode of We Tawk Funny, Sharon Pfeiffer and Joe Rubo sit down with comedian, writer and longtime Late Show talent coordinator Eddie Brill for a hilarious and surprisingly emotional conversation about his life in comedy.

Eddie takes us from his earliest comedy influences to the legendary comedy scene at Emerson College, where he crossed paths with future stars including Denis Leary, Mario Cantone and Steven Wright.

He also reveals how he went from having roughly 35 cents in his pocket and taking television warm-up gigs to getting an opportunity at David Letterman. What began as a six-week trial ultimately turned into an incredible 17-year run with the show.

Eddie shares behind-the-scenes memories of Letterman and encounters with entertainment legends including Don Rickles, Sophia Loren, Elvis Costello and Burt Bacharach. He also tells the emotional story of how Don Rickles helped change Eddie's relationship with his father after praising him on national television.

Then the conversation gets deeply personal.

Eddie opens up about discovering he had a 12-year-old son he never knew existed, meeting him for the first time after an HBO comedy show in Bryant Park, and building the relationship they still share today.

And you won't want to miss Eddie's insane story about accepting what he thought was a small $200 comedy gig for the Shriners—only to discover he was actually performing at the 8,800-seat Shrine Auditorium alongside Jimmy Stewart and Jerry Lee Lewis. After crushing in front of thousands of people, Eddie went to the Comedy Store later that night...and bombed.

In this episode:

• Eddie Brill's journey into stand-up comedy
• 17 years working with David Letterman
• What Letterman was really like behind the scenes
• Eddie's friendship with Don Rickles
• Meeting some of the biggest stars in entertainment
• Discovering he had a 12-year-old son
• The importance of vulnerability in comedy
• New York City's legendary comedy scene
• Performing for 8,800 people at the Shrine Auditorium
• Why respecting your stage time matters
• The Catskill Comedy Festival
• Eddie's advice and perspective after decades in comedy

From hilarious show-business stories to family, loss, fatherhood and the lessons learned from a lifetime of making people laugh, this episode has a little bit of everything.

Subscribe to We Tawk Funny for more conversations with comedians, entertainers and fascinating personalities with Sharon Pfeiffer and Joe Rubo.

Comment below: Who's your all-time favorite late-night host?

This week on We Tawk Funny, things don't exactly go according to plan.

When the scheduled guest can't make it, Sharon Pfeiffer and Joe Rubbo pull some strings and land someone who's normally on the OTHER side of the cameras — Podcast Junkeez producer and studio owner Ben Castro.

For the first time, Ben steps out from behind the control board and into the guest chair to tell the story of how he found his way into the podcast business.

Ben shares his unlikely journey from studying environmental engineering and working in hospitality to learning audio, video and production — eventually leaving his previous podcast studio and helping build Podcast Junkeez Studios.

The conversation gets into what REALLY goes into producing a professional podcast, why Ben believes the experience of recording in a studio matters, and how Podcast Junkeez has grown largely through relationships and word of mouth rather than simply throwing money at advertising.

Ben also explains why he'll actually turn potential podcast clients away, the red flags he looks for when someone wants to start a show, why buying followers can destroy your organic momentum, and why he refuses to sell people the dream that starting a podcast automatically means fame and money.

Plus, Sharon and Joe reflect on nearly 40 episodes of We Tawk Funny, how much the show has grown, and why podcasting has become much more than simply sitting down and talking into microphones.

And because it's We Tawk Funny, somehow the conversation eventually ends up involving swingers conventions, tight ear holes, lube, and hearing aids.

You know... a normal Tuesday.

In this episode:

• How Ben Castro got into podcasting
• The origin of Podcast Junkeez Studios
• Leaving a job to bet on yourself
• Building a professional podcast studio
• Why word of mouth has been Ben's biggest growth tool
• Why buying followers can hurt your podcast
• What makes Ben turn potential clients away
• Home podcasts vs. professional studios
• The future of podcasting and AI
• Behind the scenes of producing We Tawk Funny
• Celebrating nearly 40 episodes of WTF

We Tawk Funny is a weekly podcast hosted by Sharon Pfeiffer and Joe Rubbo that's less about the way they talk and more about what they talk about, entertainment, celebrity, comedy and culture.

What happens when the hosts become the guests?

In this special episode of We Talk Funny, Sharon Pfeiffer and Joe Rubbo turn the tables and interview each other, sharing the incredible stories behind their careers, lifelong friendship, and how We Talk Funny came to life.

From Joe's days as a child actor in The Last American Virgin, David Letterman, and Striptease to Sharon's work alongside Matthew McConaughey in The Beach Bum, the conversation is packed with behind-the-scenes Hollywood stories, comedy memories, and heartfelt moments.

They also discuss:

• The origins of We Talk Funny
• Joe's journey through television, VIP TV, and rebuilding his life
• Sharon's acting career and stand-up comedy
• Their favorite celebrity guests and unforgettable podcast moments
• The challenges, laughs, and friendships that have shaped the show
• Why this podcast has become more than just entertainment—it has become family

This is one of the most personal episodes of We Talk Funny yet, giving viewers a chance to get to know the hosts behind the laughs.

If you enjoy celebrity interviews, comedy, entertainment stories, and authentic conversations, this episode is for you.

👍 Like, comment, and subscribe for more episodes of We Talk Funny!

#WeTalkFunny #SharonPfeiffer #JoeRubbo #ComedyPodcast #HollywoodStories #BehindTheScenes #Entertainment #StandUpComedy #Actors #PodcastJunkeez

How do you turn a lifetime of pain into purpose?

On this episode of We Tawk Funny, Sharon Pfeiffer and Joe Rubo welcome award-winning writer, producer, director, and filmmaker Glenn Evelyn for one of their most heartfelt conversations yet. Glenn shares his deeply personal journey—from growing up afraid to be himself, to losing his longtime partner, surviving life-threatening health challenges, and ultimately creating the award-winning limited series Our Family Pride based on his own life experiences.

They discuss:

• The true story behind Our Family Pride
• Growing up in a strict Christian environment
• Coming out and accepting your authentic self
• Grief, loss, and surviving unimaginable tragedy
• Building an award-winning independent film
• The realities of filmmaking and film festivals
• Hollywood, storytelling, and what's next for Gunnar Max Productions
• Plenty of laughs, behind-the-scenes stories, and classic We Tawk Funny moments

Whether you're passionate about filmmaking, storytelling, personal growth, or simply love hearing inspiring conversations, this is an episode you won't want to miss.

🎬 Guest: Glenn Evelyn
🎙️ Hosts: Sharon Pfeiffer & Joe Rubbo

If you enjoyed this episode, be sure to Like, Subscribe, and hit the notification bell for more conversations with entertainers, filmmakers, comedians, and fascinating guests every week.

What does it really take to build a career in stand-up comedy?

On this episode of We Tawk Funny, Sharon Pfeiffer and Joe Rubbo welcome nationally touring comedian, actress, writer, musician, and podcast host Esther Ku for an honest, hilarious, and inspiring conversation about life on and off the stage.

Esther shares her journey from performing stand-up in New York to appearing on Last Comic Standing, The Howard Stern Show, and Wild 'N Out, while discussing the realities of chasing success in comedy. The conversation covers everything from dealing with online critics and writing new material to the rise of Kill Tony, moving from New York to Miami, podcasting, music, and finding your own creative path.

Whether you're a comedy fan, an aspiring comedian, or simply enjoy behind-the-scenes stories from the entertainment industry, this episode delivers plenty of laughs, insight, and valuable advice.

• Esther Ku's stand-up comedy journey
• Last Comic Standing, Howard Stern & Wild 'N Out
• The evolution of comedy and Kill Tony
• Handling online criticism and hecklers
• Writing new material and performing live
• Life in New York vs. Miami
• Music, podcasting, and creative careers
• Behind the scenes of being a professional comedian

Subscribe to We Tawk Funny for weekly conversations with comedians, actors, entertainers, and industry professionals who share the stories behind the laughs.

In this episode:

What does it take to cast some of Hollywood's biggest movies and television shows?

This week on We Tawk Funny, Sharon Pfeiffer and Joe Rubo welcome legendary South Florida casting director Ellen Jacoby, whose remarkable career has helped shape Hollywood for nearly four decades.

From casting iconic productions like Miami Vice, The Birdcage, The Truman Show, Rock of Ages, Striptease, and countless other films and television shows, Ellen shares incredible behind-the-scenes stories about working with some of the biggest names in entertainment.

But that's just the beginning.

Ellen opens up about her fascinating life outside of casting—from becoming one of the world's top professional backgammon players and befriending Lucille Ball, to meeting Johnny Carson, touring NASA with Jim Carrey, wrestling an alligator with the Seminole Tribe, and helping fight to bring the film industry back to Florida.

As always on We Tawk Funny, the conversation is filled with laughs, unbelievable stories, and unforgettable moments.

• Ellen Jacoby's journey into Hollywood casting
• Behind-the-scenes stories from Miami Vice, The Birdcage, The Truman Show, Rock of Ages, and more
• Working with Robin Williams, Nathan Lane, Jim Carrey, Tom Cruise, Mike Nichols, and other Hollywood legends
• Ellen's friendship with Lucille Ball
• Celebrity backgammon tournaments and unexpected adventures
• The fight to bring film production back to Florida
• Advice for actors looking to break into Hollywood
• Why social media has changed casting forever
• Avoiding casting scams and industry pitfalls
• Funny, heartfelt, and unbelievable stories from one of Hollywood's most accomplished casting directors

If you love Hollywood, classic movies, celebrity stories, and conversations that are equal parts hilarious and fascinating, you won't want to miss this episode.

Don't forget to Like, Subscribe, and Share for more unforgettable guests, behind-the-scenes stories, and plenty of laughs on We Tawk Funny!

In This Episode:

This week on We Tawk Funny, Sharon Pfeiffer and Joe Rubbo welcome award-winning entertainer Maryann Maisano for an unforgettable conversation filled with laughter, music, and incredible Hollywood stories.

Maryann shares how a chance encounter led to a friendship with legendary actor Danny Aiello, the remarkable story behind their Grammy-nominated song "City of Light," and how she built a career as a singer, songwriter, playwright, comedian, and creator of the hit comedy show The Italian Chicks.

From outrageous family stories and life in an Italian household to stand-up comedy, theater productions, and unforgettable moments in show business, this episode is packed with humor, heart, and inspiration.

In this episode:

• Maryann Maisano entertainment journey
• Working with Danny Aiello
• The story behind the Grammy-nominated "City of Light"
• Creating The Italian Chicks
• Life as a singer, songwriter, and playwright
• Stand-up comedy and unforgettable stage moments
• Italian family stories that inspired her writing
• Breaking into the entertainment industry
• Funny behind-the-scenes stories from theater and comedy
• Why creativity and persistence never go out of style

If you love comedy, music, storytelling, Broadway, Italian culture, and behind-the-scenes Hollywood stories, you won't want to miss this hilarious and heartfelt conversation.

Guest:
Maryann Maisano – Singer • Songwriter • Comedian • Playwright • Creator of The Italian Chicks

On this episode of We Tawk Funny, Joe Rubo and Sharon Pfeiffer welcome entertainer extraordinaire NIKKO—DJ, comedian, actor, MC, breakdancer, drummer, and founder of NIKKO Nation—for a hilarious conversation about life in the entertainment business.

From hosting celebrity events and luxury car shows to performing at weddings, bar mitzvahs, cruises, and corporate parties, NIKKO shares unforgettable behind-the-scenes stories from over 35 years of entertaining audiences across the country.

In this episode:

• How NIKKO built a career in live entertainment
• Behind the scenes of weddings, bar mitzvahs & corporate events
• The craziest party stories you'll ever hear
• DJ life then vs. now
• Acting, comedy, and performing on stage
• Breakdancing and music careers
• South Florida's entertainment scene
• Car shows, motorcycles, and celebrity events
• Starting stand-up comedy
• The importance of energy and connecting with an audience
• Hilarious stories from decades in entertainment

Packed with laughs, outrageous stories, and nonstop energy, this episode is a celebration of live entertainment, comedy, music, and doing what you love. Whether you're an entertainer, musician, comedian, event planner, or simply looking for a great laugh, this episode is guaranteed to keep you entertained from start to finish.

On this episode of We Tawk Funny, Sharon Pfeiffer and Joe Rubbo welcome filmmaker, producer, director, actor, and entrepreneur Aaron Abelto, along with actor and producer Woody Deant, for an entertaining conversation about independent filmmaking, creativity, Hollywood, and the growing impact of AI on the entertainment industry.

The discussion covers Aaron's journey from background actor to award-winning filmmaker, the challenges of producing independent films, and the upcoming premiere of Hypersonic, a new action-thriller series debuting on Apple TV and Amazon Prime. Aaron and Woody share behind-the-scenes stories from production, lessons learned in the film business, and what it takes to build a successful career in entertainment from South Florida.

In this episode:

• The rise of independent filmmaking
• South Florida's growing film industry
• AI's impact on movies, writing, and creativity
• Why authentic storytelling still matters
• Producing and financing independent films
• Behind-the-scenes stories from film sets
• The making of Hypersonic
• Working with streaming platforms
• Acting, directing, and producing
• Building a career in entertainment
• Hollywood vs. independent film
• Future projects and industry trends

The conversation is packed with laughs, industry insights, movie stories, and a passionate debate about whether artificial intelligence can ever replace true human creativity.

If you love movies, filmmaking, entertainment, streaming series, or hearing the real stories behind the camera, this is an episode you won't want to miss.