True self

The rise and fall of Long Island’s famed ‘Tupperware Queen’

Once upon a time, Jennifer Bobbi was known as Long Island’s famed Tupperware queen. She sold hundreds of thousands of dollars’ worth of kitchenware, raking in a hefty six-figure salary along the way.

Bobbi was known to her clients as Aunt Barbara, a drag queen who dressed in 1960s-era getups, lots of makeup, and a black bob wig. Her sales pitch included lots of attitude and sassy comebacks.

“Most people thought it was a great, fun thing to do in their house,” 48-year-old Bobbi tells ABC News in a new documentary short. “It was a comedy show, but it was a comedy show in their minds because it was a man dressed as a woman playing a character.”

Related: LCD Soundsystem’s Gavin Russom comes out as trans: “I’m the happiest I’ve ever been”

Over the years, Bobbi became so successful selling Tupperware that she earned cash bonuses, cars, and trips to Hawaii, Florida, and New Orleans. She appeared on several local television programs and developed a strong social media following.

But unbeknownst to her clients and fans, there was something much deeper going on underneath the hair, the makeup, and the false eyelashes. From a very young age, Bobbi had known she was a woman.

Two years ago, Bobbi decided to drop the act and begin living her life openly as a woman. Almost immediately, she noticed a change in how her clients treated her.

“I thought that, well, they accept Aunt Barbara. Why wouldn’t they accept me? I’m just the person who’s behind Aunt Barbara,” Bobbie recalls.

Unfortunately, that wasn’t the case. Many of her longtime customers stopped buying products from her and canceled their Tupperware parties.

Related: Cold case, real life: Who killed the transgender woman & activist, Marsha P. Johnson?

“I do think that my transition was a major contributing factor to the decline in my business,” Bobbi says. “I noticed that some people don’t understand the difference between what they perceived as a drag queen or as being transgender or a cross-dresser.”

Earlier this year, Bobbi came close to bankruptcy; business had “dried up.”

“I was able to have a good standard of living, and that went away, just slowly went away, little by little. Things got harder,” she says. “Eventually, I wasn’t able to pay for basic necessities.”

Sadly, this sort of thing is not uncommon. According to, one in four trans people have lost a job due to bias, and more than three-fourths have experienced some form of workplace discrimination.

“It’s funny–it’s all fun and games when you’re perceived as a man dressing as a woman but you don’t want to be a woman,” Bobbi says. “But when you’re biologically a man and internally and innately you’re a woman, then it’s not so funny anymore.”

She managed to find work as an executive assistant at a nonprofit and as the caregiver for an individual with disabilities, but she earns just a fraction of what she made before her transition.

Related: Comedian refuses to apologize after proudly saying he’d kill a trans woman

“I didn’t ask for this. No person that’s transgender asks to be transgender,” Bobbi says. “I would love to continue being who everyone wants me to be or needs me to be or thought I was, but I can’t.”

“I have to be true to myself. I have to be who I am. I’m the one who’s going to be living the rest of my life.”

Watch the moving documentary HERE.

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  • kurt_t

    I don’t think Bobbi’s gender identity has much to do with the downturn in her Tupperware business. I think it’s more likely she’s a victim of Internet disruption. You can buy Tupperware online these days, either directly from the manufacturer or from an online retailer.

    Now back in my day, if you wanted Tupperware, you had to go to a Tupperware party. Or throw one. Which I did. In 1991. It was a blast. But you think my kids would go to a Tupperware party? Even one emceed by a wisecracking Long Island housewife in vintage rayon? No. They’re too busy with their Warcraft and their Netflix.

    I notice that Aunt Barbara has a Youtube channel, so it looks like she’s headed in the right direction. Maybe she can teach the young people how to mold Jell-O. Man, you want to talk about a lost art.

    • Brian

      She transitioned 2 years ago, it has nothing to do with the internet.

      Drag queen Tupperware parties are basically a way for people to get a drag show in the comfort of their own homes. It’s about the drag queen, not the Tupperware. When you take the drag queen out of the equation, it becomes just a woman selling Tupperware, AKA boring.

      I assume after she transitioned she stopped doing the parties as a drag queen, otherwise I don’t see how anyone would have known the difference. If you take out the element that people are hiring you for, yeah, it’s gonna affect your business. She is a performer, there is no reason she couldn’t have continued doing the character for work after transitioning in her personal life.

    • kurt_t

      “just a woman selling Tupperware, AKA boring”

      See? You sound just like my kids.

  • Bob LaBlah

    “It’s funny–it’s all fun and games when you’re perceived as a man dressing as a woman but you don’t want to be a woman,” Bobbi says. “But when you’re biologically a man and internally and innately you’re a woman, then it’s not so funny anymore.”

    Dear, that notwithstanding it sounds like you clearly didnt look down the road and ask yourself was it really necessary to tell then your business. I can see the reactions of many of your customers when you just HAD to let them know that. Society is cruel and that is why it is always more important to consider how you are going to support yourself once you become your inner self while knowing the possible consequences. I really do wish the article listed the year all of this happened. With Family Dollar, Dollar Tree and Dollar General all selling microwaveable Rubbermaid products for less than five dollars the competition Tupperware has to deal with makes me wonder how did you make that kind of money for so long.

    • DarkZephyr

      She clearly thought that they would all be accepting of her. Nobody LGBT likes being in the closet all the time when they have finally decided to be true to themselves and come out.

    • Bob LaBlah

      I couldn’t agree more with your last sentence about being in the closet but when you come out of the closet as she did not taking into account the possibility of loss of business I question whether that was the correct thing to do. It appears not to be in this case IF she was making what she was making (which some how I strongly doubt).

    • DCguy

      It isn’t telling them her business when she is just walking outside the house.

  • bbg372

    What makes Jennifer think they do not accept her? It seems to me they understand perfectly the difference between a drag performer and a transgender person. Hence, why they no longer consider her parties a comedy show now that she is openly transgender. It shows they take her trans identity seriously, that they do not consider it a joke. Her problem, is that her success was due to the novelty of combining a drag show with a Tupperware party. Changing the formula of her success is why her business slowed, not transphobia.

    • DarkZephyr

      What makes you think her jokes were related to drag? She probably still did the comedy.

  • Ummmm Yeah

    Or everyone that bought Tupperware died of old age.

    • kurt_t

      For that you get my Rip Taylor Face. The one where he’s looking sideways with his eyelids halfway down and his mouth in the “O” position.

  • captainburrito

    Should have invested the money while it was good.

    • kurt_t

      For all we know she bought Beanie Babies.

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