Backstage Pass: The Night I Met My Childhood Heroes
The night back in 2001 when Lance Bass orchestrated a dinner between Debbie Gibson and Tiffany, and somehow, we ended up singing karaoke with Vince Vaughn.
This is a story I usually save for dinner parties, but inspired by last week’s Two Truths and a Lie, I figured it deserved its own post—in all of its crazy detail. Thank God I kept a journal, because every part of this story is true. In all its ridiculousness, I had forgotten many details—some of which even floored me as I transcribed them to share.
Picture it: Hollywood, 2001.
Two '80s pop princess royalty who’d spent their careers avoiding each other because the media convinced them they were rivals—and one determined boy band superstar who wanted to settle it once and for all. I’m talking about the night Lance Bass orchestrated a dinner between Debbie Gibson and Tiffany, and somehow, we ended up singing karaoke with Vince Vaughn.
Life in the late '80s wasn’t exactly a walk in the park for me. I had a whole list of quirks that made fitting in feel impossible. My mom? She wasn’t winning any parenting awards. A frequent partygoer who was either out most of the time or not exactly the kind of company you wanted when she was home. She decided I should skip second grade when we moved from California to Washington, but that wasn’t something the other kids at the many schools we bounced around to knew. I was a monet from an early age. I was smart and tall enough to visually blend in with the boys from afar, but up close you’d realize my body wasn’t on the same page—it lagged behind, my voice octaves too high and the only hair on my body beside my head was on my eyes, leaving me underdeveloped and the odd one out, freakish for my perceived age. Additionally , I was inately shy (which, of course, translated to “effeminate” in the eyes of others), and I became the perfect target for bullies. Making friends was hard, and each day at school felt like competing in the Survival Olympics.
But every afternoon, when I got home from school, I knew I could finally breathe. With no mean kids in sight and my mom nowhere to be found, it was time for my daily transformation. I had a routine: I’d grab one of my three prized VHS concert tapes and turn my living room into the world’s greatest stage. My mom’s closet became my wardrobe department, and the furniture was my set. Side and coffee tables were strategically moved to create platforms and stages. Lampshades were removed to create silhouettes behind sheets. I had Madonna: Who’s That Girl? live from Italy, The Go-Go’s: Wild at The Greek, and, of course, Debbie Gibson: Out of the Blue Tour live from Pittsburgh. For 90 minutes every afternoon, I wasn’t just some shy 13-year-old kid in Everett, Washington—I was the hottest performer on the planet, nailing every move, every breath, and even the crowd-hyping banter between songs. To this day, I can still tell anyone, “It is a pleasure to be here in the homeland,” in Italian.
When people ask me how I stayed so positive despite all the curveballs life threw my way, I always credit two people: Madonna and Debbie Gibson. My mom might not have been around to teach me much, but that was okay. I had Madonna exposing me to art, social causes, critical thought, and, you know, all that motherly stuff like how to drink from a glass Evian bottle and strike a pose. And then there was Debbie—my cool older sister figure—always there to remind me not to let life get me down and that anything is possible.
Fast forward a decade, to my mid-twenties—a well-rounded young adult with a budding life in Hollywood. One Sunday morning, after a few too many mimosas with one of my best friends Wendy, we turned her living room into a full-on Debbie Gibson dance studio. I taught her all the choreography to Electric Youth like I was back on tour in my living room and if memory serves, my friend Denny dislocated his knee during the big dance bridge.
For some backstory, Wendy was producing films with Lance Bass (which, in a story for another day, is part of how our friendship began), and he had just come off tour with *NSYNC, where Debbie Gibson had been opening for them. Lance was somehow friends with Tiffany’s friend Ron, and somewhere in there, there was also a tie to Reba McEntire. But let’s stick to this story for now. Suffice it to say, that’s how everyone was connected.
From what I remember, Debbie and Tiffany had always assumed the other didn’t care for them, largely thanks to the way the media often pitted them against each other. But Lance, knowing both of them, realized they would actually love each other if they met, so he organized a group dinner to bring them together. While I wasn’t there for the dinner—I was lucky enough to be part of the aftermath.
By everyone’s recollection, Wendy (who, from day one, has been my biggest hype woman) couldn’t stop gushing to Debbie about me throughout the entire dinner. She told her all about how much much she meant to me, how I knew all of her lyrics and choreography, and even shared stories from our recent dance party. Thankfully, Lance was there to back up Wendy’s story—otherwise, Deb might’ve been tempted to file a restraining order!
Meanwhile, across town, I was at dinner with my roommate Laura unaware any of this was happening. When we got home, there was an urgent message waiting on the answering machine (remember life before cell phones?) from Lance and Wendy: “Where are you? You need to get over to the L’Ermitage immediately. Don’t ask questions.”
We rushed over and arrived around 10 p.m., Lance, practically bouncing with excitement, met us at the door: “Bob, you are not going to believe this!” Wendy handed me a napkin with a bold lipstick kiss and a handwritten note that read:
“And that’s not all,” Wendy squealed. “She’s at the bar, waiting to meet you! Let’s go!”
First came the shock, then the tears. “I can’t. I can’t meet her. No way.”
Spoiler: I could.
We arrived at Micky’s—the premiere gay nightclub in West Hollywood at the time—where Tiffany’s friend Ron greeted us with, “Oh, you must be Big Gay Bob! I expected fireworks to shoot out of your head based on how much Lance and Wendy talked about you!” Did he really have to call me big? And what could they possibly have been saying about me to make him say that?
I’d also like to pause here and point out that this was five years before Lance publicly came out, and was right at the height of *NSYNC's popularity. But that’s the kind of friend he is and has always been—he knew how much this meant to me and didn’t care what anyone might think about him being seen at a gay club.
As we made our way to the dance floor, everyone was introducing themselves, and then—there she was. Debbie Gibson. She spotted me and shouted, “BOB!!!” like we were old friends, before giving me one of the best hugs of my life. Just when I thought the night couldn’t get any more surreal, Lance introduced me to Tiffany—yes, the Tiffany, who ruled every mall in America and knocked Michael Jackson off the charts in 1987.
In my mind, I was cool and matter-of-fact, but in reality, I was a Motorola flip phone trying to run on an iPhone operating system, and gibberish became my primary language.
We all danced to Destiny’s Child’s Charlie’s Angels theme song, and then Debbie had to head out. One and done. She had only come long enough to meet me. Pinch me!
Before she left, Debbie gave me another hug and said, “Bob, it was really great to meet you,” and then she was off. Which was probably for the best, because even though I had so much I wanted to say to her, my brain had completely short-circuited by then.
As we headed off to a private area, I sat off to the side by myself, trying to process everything that had just happened. Suddenly, I felt a playful thwap across my arm. Tiffany sidled up on the stool next to mine, straight-faced and with a low tone, said, “Bob, we have issues.”
“You and me? How could we possibly have issues?”
After sitting through an entire dinner listening to everyone bloviate over Debbie and not mentioning a single word about her, Tiffany had reached her limit. “What’s up with you being Deb’s biggest fan? I had a hit album out that same year!”
It was so disarming, charming, and downright hilarious that I couldn’t stop laughing. That moment sums up Tiffany perfectly—scrappy, wickedly funny, and unafraid to call you out. From that point on, I was in love with Tiffany—not just the singer, but my new friend—and we’ve been close ever since. However that night, she didn’t let me off the hook easily. I spent the rest of the evening awkwardly trying to dig myself out of the hole (a hole dug by Lance and Wendy, mind you), recounting favorite moments of her career while promising to buy her new album and tickets to her upcoming show.
To really date this story, Lance got a message on his Skytel pager from our friend Sarah, who had rented us a karaoke room, where she was waiting with Vince Vaughn. (Yes, that Vince Vaughn.) The night was a blur, yet one I’ll never forget. We couldn’t have been there more than 10 minutes before Vince convinced Tiffany to sing her iconic hit I Think We’re Alone Now. And to her credit—and our utter disbelief—she belted it out without hesitation like we were in a sold-out arena, not a tiny 10’x10’ glass room.
That’s another reason I love her—Tiffany doesn’t take herself too seriously. She didn’t even hesitate when Vince asked. Years later, she did the same thing at a dinner party at my house, forever cementing her as the coolest.
After many songs (and a few unfortunate moments—like when I left poor Lance high and dry singing all the male parts from Summer Nights from Grease because I instinctively gravitate toward Olivia Newton-John’s parts), we finally called it a night at 4:00 a.m.—yes, on a school night. Before Tiffany left, I promised her I’d buy her new album the next day (which I did). She gave me a playful “whatever,” but I hugged her extra tight and slipped her my number anyway.
How could I possibly explain any of this to my 13-year-old self? It’s never been lost on me that none of this is normal.
This next part is straight out of my journal, and 50-year-old me is absolutely horrified by 20-something me, but I’m sharing it anyway. As Vince was saying his goodbyes, he shook my hand and said, “Nice to meet you.”
In an unwarranted moment of chutzpah, I replied, “Actually, we met at a Halloween party a couple of weeks ago.”
With perfect sarcasm, he responded, “Oh yeah, the one with all the costumes?”
“I was the wizard you kept fighting with for cocktails at the bar.” Full disclosure: I remember this exchange at the karaoke bar, I remember the Halloween party, and I vaguely remember being in line with him arguing about drinks. But for the life of me, I have no idea what it was about—or what possessed me to bring it up.
“Oh. Well, who won?” he asked with a smirk.
“Me, of course.” And then… I WALKED AWAY. I just marched right back into the karaoke booth! Who did I think I was?!
A few days later, as if this story wasn’t absurd enough, our friend Mika, who was working on the Planet of the Apes remake, mentioned she could give us a tour of the set since they weren’t shooting that day. It was a Saturday afternoon, and she invited Lance to join. But since *NSYNC was filming their Super Bowl promos with Ben Stiller on the same lot, it only seemed polite to bring the whole group along—and their security, and possibly Ben Stiller (I honestly can’t remember).
At some point during the tour, Chris Kirkpatrick was on the phone with Deb, who had planned to join us with Tiffany for dinner. Something came up, and she had to cancel, but Chris, knowing the story from a few days earlier, handed me the phone. This time, I was much more composed and finally got to say what I had hoped that night (not knowing if I’d ever have the chance again). I was able to thank her and share how much she had meant to me during my adolescence. Expressing gratitude felt so much more sincere than trying to prove I knew all the lyrics to Shock Your Mama.
At dinner, I told Tiffany I’d bought her new album and raved about my favorite tracks and she gave me the biggest hug. Before long, we were trading beauty secrets (did you know olive oil is great for dry skin?) and making plans to hang out again. (Yes, that olive oil revelation came straight from my journal and felt much more groundbreaking 23 years ago!)
And that, my friends, is the origin story of how I became friends with Debbie Gibson and Tiffany. Or is it Tiffany and Debbie Gibson? I’ve learned not to play favorites—loving them both equally is key.
Also, my journal reminded me of one more thing that happened a week later. Sarah invited me to an Elvis Presley tribute at the House of Blues—lots of pompadours, rhinestones, and people fully living their Elvis fantasy. And once again, who should I end up sitting next to? Vince Vaughn. He leaned in with a grin and said, with extra emphasis, “It is so good SEEING you again.”
I smiled back, equal parts delighted and totally mortified.
BONUS: As mentioned, when I was 13, I would perform live from my living room in Everett, Washington, with three VHS tapes as my backing band. One of them was The Go-Go’s: Wild At The Greek, where I was Belinda Carlisle—and you couldn’t convince me otherwise. There is no exaggeration when I say that, in 2011, when the sweet and fabulous Jane Wiedlin invited me onto the actual Greek Theatre stage to dance during Cool Jerk, right next to Belinda Carlisle, I left my body. In a different setting, I might be embarrassed to share this video, but here, it perfectly captures another pinch-me moment!
OMG what a trip! I had dislocated my knee before this event. I was sitting down with my leg propped up while watching Debbie do her thing when I suddenly remembered... this woman has been part of my knee saga before! From now on ... I will call it ... Debbie Knee. Thanks for the memories, Bob!
What an epic night this was! I am so glad you wrote details in your journal because I had completely forgotten some of this, but I will never forget how excited everyone was that you finally got to meet her.💗 I do remember riding around in “Satchel” listening to both Debbie’s and Tiffany’s new albums after that night.