Barbra Streisand's Most Out-Of-Pocket Moments

Barbra Streisand has spent decades as one of the most celebrated and recognizable figures in entertainment. That kind of longevity and success typically doesn't happen without talent, drive, luck, and strong personality. In Streisand's case, that personality often takes center stage in ways that surprise even her most devoted fans.

Whenever we see Barbra Streisand, be it on screen or on stage, she's the epitome of grace and elegance. But alongside her achievements, Streisand has developed a reputation for being, at times, eccentric, to say the least. Whether it's her candid public statements or her tendency to, for better or worse, challenge expectations, she has never been someone who blends quietly into the background. Instead, she'll forever be known as a bold and envelope-pushing Hollywood legend.

Part of what makes her so compelling is that you never quite know what she'll do or say next. That unpredictability has led to moments that feel relatively out of pocket. Streisand doesn't shy away from mixing it up, and her willingness to color outside of the lines only adds another layer to an already one-of-a-kind public persona.

As any dog lover knows, losing a pup is nothing short of heartbreaking. Barbra Streisand's way of dealing with the death of her dog was on another level. In 2017, Samantha, Streisand's Coton de Tulear, died. Samantha was succeeded by Miss Violet and Miss Scarlett, two Coton de Tulears who look just like Samantha... and there's a reason for that. Both pups are clones of Streisand's late dog. As she shared in a 2018 interview with Variety, cells were obtained from Samantha and used to create Miss Violet and Miss Scarlet. The clones were born the same year Samantha died. 

What made the whole endeavor all the more mind-blowing was how Streisand presented the news rather matter-of-factly. She didn't treat the clones as a strange or secretive experiment, and didn't seem too concerned about possible criticism. Instead, she introduced them to the world with a kind of pride and affection that made it clear they were meant to carry on a legacy. Funny enough, as far as she's concerned, Violet and Scarlett are not exactly like her precious Samantha. "They have different personalities," Streisand noted to Variety. "I'm waiting for them to get older so I can see if they have her brown eyes and her seriousness."

There's something undeniably fascinating about the blend of deep emotional attachment and cutting-edge technology. For some, it came across as a potentially questionable way to grieve; for others, it raised questions about ethics, identity, and the limits of science.

Barbra Streisand has made a lot of power moves throughout her career, but this one might be one of the biggest. Whether it was a personal pet peeve or simply her need to control her public image down to the last detail, Streisand took it upon herself to correct one of the biggest tech companies on the planet. After she realized that Siri, Apple's virtual assistant, was slightly mispronouncing her last name, she did not shrug it off or ask an assistant to work it out with the company's PR team. Instead, she took matters into her own hands and got results.

"She pronounces my name wrong," Streisand told NPR in 2016. "Streisand with a soft S, like sand on the beach. I've been saying this for my whole career." She proudly went on to explain how she went straight to the top. "What did I do? I called the head of Apple, Tim Cook, and he delightfully agreed to have Siri change the pronunciation of my name, finally, with the next update on 30 September. So let's see if that happens because I will be thrilled," she said. Barbra Streisand's name is a carefully curated part of her brand, so while a virtual assistant's mispronunciation might seem like no big deal to most of us, it makes sense that she would go to such lengths to make sure Siri gets it right.

No one would bat an eye at a rich celebrity owning an extravagant mansion. But there's a difference between a spacious walk-in closet and your own personal shopping mall. Underneath Barbra Streisand's Malibu abode, there's an entire underground shopping street. Yes, she has a fully realized, old-timey promenade designed to house and display her personal collections. It's part museum, part secret room fantasy, and maybe a little surreal. It blurs the line between luxurious and bizarre. 

The singer's custom-built shopping street is not just to house her collection of designer clothes. She also has a candy store, a doll display, and different antiques she collects. She walks the cobblestone streets of her private mall both to decide what to wear and to admire the treasures she's acquired throughout her life.

Streisand's basement emporium has long been the stuff of legend, even inspiring Jonathan Tolins' 2013 play "Buyer & Cellar." Over the years, she has offered media outlets tours of the space, including a 2023 segment featured on "The Late Show with Stephen Colbert."

While she certainly isn't the only celebrity who takes her angles seriously, Barbra Streisand has a long history of going to great lengths to make sure only the left side of her face is photographed. In 2017, for example, Streisand reportedly was so adamant that only her "good side" was photographed when she arrived at a charity telethon that she totally disregarded the flow of the red carpet. "There were a ton of celebrities on the red carpet, but she wanted to walk the carpet in reverse order, so the cameras would only shoot her good side. It was as if she was a salmon swimming upstream," a source claimed to Page Six.

Streisand also famously prefers sitting on a certain side of the stage when she goes on talk shows — so much so, that she apparently won't go on the show unless she's given her seat of choice. Some hosts will oblige, but as Jimmy Kimmel said on "Watch What Happens Live," she ultimately skipped his show because he wouldn't swap seats with her. "The condition was we couldn't talk about the fact that we'd switched around, and I was like, 'I just don't see how that is going to work,'" he said.

Speaking to the Daily Mail in 2014, Streisand opened up about why she prefers her left side to her right. "I have two different sides of my face. ... From certain angles, maybe I am beautiful. From others I am horrible," she stated. "So that's the truth. That's my truth anyway." 

Decades before the Super Bowl XXXVIII halftime show gave us the term "wardrobe malfunction," Barbra Streisand had a sartorial snafu of her own. In 1969, she received her first Oscar for her unforgettable performance in "Funny Girl." As Streisand headed to the stage to accept her award, she looked polished and chic in a black and white glimmering ensemble by Arnold Scaasi. But once she reached the stage, the seemingly elegant garment was suddenly a lot more sheer than anyone, including Streisand, expected.

"I had no idea that when the lights hit that outfit, it would become transparent!" the singer explained to W magazine in 2016. "I wanted a white collar and cuffs, which it had, and I wore my hair under my chin, because I thought to myself, I'm going to win two Oscars in my lifetime, and I'll be more conservative next time."

Eight years later, Streisand did indeed receive her second Oscar. And yes, she went with a much more conservative look, wearing a high-neck burnt orange tiered gown that she designed herself. The pleated material was indeed opaque.

At a point in her career when most artists would rely entirely on traditional promotion, or not bother at all, Barbra Streisand took a decidedly unconventional approach. In 2012, she called into home shopping network QVC to sell her own album directly to viewers.

Over the phone, she spoke with host Jonathan Redford — cousin of her "The Way We Were" co-star Robert Redford — and Richard Jay-Alexander, who were plugging her album "Release Me." Streisand noted that while a lot of the songs on that album were songs her fans had already heard, this is the first time she's included them on an album. When asked why they didn't make the cut in the past, she gave a signature Streisand answer.

"I was always more finicky earlier on. If I didn't like one note I didn't release something, but they're pretty good," she stated (via Barbra Archives). However, she ultimately decided that the songs didn't need to be flawless to be good. "Whatever flaws I think they have ... I'm just leaving them there. I'm less demanding now, more forgiving of myself. It's my work and I wanted to share it with the public." Finally, she joked about buying her own album through QVC: "I worked on this album for a long time, I don't even have a copy. Can I buy one?"

Sometimes, the most lasting impact a celebrity has on culture comes from a moment that doesn't go according to plan. That's exactly what happened when Barbra Streisand unintentionally created what is now known as the "Streisand effect." 

In 2003, Streisand took legal action against a photographer who included a photo of her cliffside Malibu home on a website. The lawsuit stated that she believed that the picture was a threat to her privacy and security. However, the person who took the picture, photographer Kenneth Adelman, apparently didn't realize whose house was in the shot. Rather, he took the picture for a project related to coastal erosion. "Mr. Adelman is not a paparazzo. He's not doing this for profit, or stalking anyone," his attorney said at the time, per the Los Angeles Times. "He is engaged in a public-interest effort to document the entire coast to preserve it from degradation. He's not about to carve out exceptions for celebrities who don't want to be identified as owning coastal land."

Before she filed the lawsuit, no attention had been drawn to the fact that the house belonged to Streisand. The picture of her house had only been downloaded six times — two of those being by her attorneys — before the lawsuit. But once her legal action became public, people swarmed to the site to download it. The phrase "Streisand effect" soon emerged as shorthand for exactly this phenomenon: when efforts to suppress something end up making it more visible.

When Barbra Streisand decided to bring Elvis Presley back for a legendary duet, it was not the first posthumous duet in music history,  but it certainly was major. After all, had things gone differently, it wouldn't have been the two superstars' first duet: Back in the 1970s, The King turned down working with Streisand on another project. 

According to Elvis' ex-wife, Priscilla Presley, Streisand wanted him to star in 1976's "A Star is Born." Elvis was initially interested, but his manager convinced him it wouldn't be good for his career. "Barbra had offered him the part," Priscilla told People. "Colonel [Tom Parker] talked him out of that saying, 'Oh, it's not going to be good. She's going to be in charge, not you. Her movie, not yours.' Elvis regretted that because he felt he could have played that part." Although Elvis never got to sing with her while he was alive, this virtual duet of "Love Me Tender" finally made this collab happen.

Live television is supposed to be all about spontaneity. What happens in the moment is what the audience gets, right? Well, when it comes to Barbra Streisand, not quite. The perfectionist singer has, at times, pushed back against the very idea of "live" by insisting on multiple takes to get a performance just right.

Barbra Streisand is a known perfectionist, and she's fine with it. In an interview with Parade, she admitted, "I never hear the good things about me." The 1994 Anaheim live recording proves this. During that show, she asked the audience a few times to redo a song she had just sung because she felt she could have done better. She began "What Are You Doing the Rest of Your Life?" by singing at the top of the stairs, but after two lines, she stopped the orchestra and said, "I don't like it up here, let's do it down there." She then jokingly told the audience she hoped it didn't ruin "the illusion" for them.

Even so, she knows that true art isn't perfect. "Really, there's no such thing. The only perfection is imperfection, because otherwise it would be inhuman, too cold," she reflected.

When Barbra Streisand signed on to do "Carpool Karaoke" with James Corden in 2018, it had all the ingredients for a viral moment: a legendary singer, a relaxed setting, and a format designed to bring out a different side of its guests. And in many ways, it delivered, just not always in the smooth, easygoing way usually associated with the segment.

From the start, Streisand didn't lean into the segment's typical carefree, sing-along vibe. Rather, she questioned the logistics, the route, and even the premise itself, creating moments that felt more self-aware than spontaneous. 

At one point, Streisand asked the host if it was necessary to listen to music... in a karaoke show. She also casually mentioned, while getting behind the wheel, that she had failed her driving test while trying to get her license renewed, and that she was a very nervous driver. It was a slightly awkward but incredibly funny video to watch.

In 1977, Barbra Streisand won her second Oscar, but not in an acting category. She took home the Academy Award for best original song for "Evergreen," which was the theme song for the second remake "A Star Is Born." Streisand starred opposite musician and actor Kris Kristofferson.

In 2018, yet another remake of the movie hit theaters, this time with Lady Gaga and Bradley Cooper in the lead roles. While Streisand acknowledged Lady Gaga and Cooper's talent, she felt the film was ultimately too similar to her version. When Streisand first learned there'd be another "A Star Is Born," she hoped for a new spin on the material, but was let down by the end result.

"At first, when I heard it was going to be done again, it was supposed to be Will Smith and Beyoncé, and I thought, 'That's interesting. Really make it different again — different kind of music, integrated actors.' I thought that was a great idea. So I was surprised when I saw how alike it was to the version that I did in 1976," the singer told The Sunday Project. She then added, "I can't argue with success, but I don't care so much about success as I do originality." Ouch.

Following the 2026 Oscars, Jane Fonda didn't mince words about Barbra Streisand's tribute to Robert Redford during the ceremony. In a red carpet interview, the "Grace and Frankie" actor questioned why Streisand did the tribute and not her, when Streisand only did one movie with Redford and Fonda did four.

Fonda and Streisand's history is... complicated. In 2016, in an interview with The New York Times, Streisand implied Fonda owes her because she turned down roles in "They Shoot Horses, Don't They?," "Klute," and "Julia." Those parts went to Fonda instead, and she won her first Oscar for her performance in "Klute." "I made Jane Fonda's career," she claimed.

On a 2020 episode of "Watch What Happens Live," Fonda offered host Andy Cohen her rebuttal to Streisand's aforementioned remarks. "She needs to say things like that to kind of, you know, give her a little boost," she told Cohen. "You have to feel sorry for her. It's been a tough life. She needs something to boost her up." Streisand clearly has no qualms about starting feuds, and this love of chaos is precisely what draws a lot of people to her.

To finish up this list, we have one of the more clumsy exchanges in Barbra Streisand's career. In 2024, Melissa McCarthy posted a photo of herself with director Adam Shankman. Streisand, who collaborated with McCarthy for her 2016 album, "Partners: Encore," and always had a friendly relationship with her, commented on her post, sending her regards to Shankman and, in a completely unexpected turn, publicly asked McCarthy if she was on Ozempic. This sparked a lot of chatter online, as some found Streisand's comment to be inappropriate, whereas others thought it was unintentionally funny and relatively harmless.

Shortly after, Streisand deleted the comment and apologized on Instagram. "OMG — I went on Instagram to see the photos we'd posted of the beautiful flowers I'd received for my birthday! Below them was a photo of my friend Melissa McCarthy who I sang with on my Encore album. She looked fantastic! I just wanted to pay her a compliment. I forgot the world is reading!" Yes, unfortunate social media gaffes can happen to anyone — even living legends. 

For the record, McCarthy got a kick out of the comment. "The takeaway, Barbra Streisand knows I exist," she said in an Instagram video. "I win the day."