Since it’s beginning, Disney Channel has thrived off of constant toxic love triangles between co-stars. More often than not, two teen pop superstars fighting over one heartthrob. But today’s story is the biggest rise and undoubtedly the darkest fall of any Disney love triangle, as it was the only one to play out across social media.
Today, I’m diving into the chaotic love story of Olivia Rodrigo and Joshua Bassett. How they fell in love on the High School Musical reboot main stage, but also broke up in front of the entire world when Joshua was rumored to have cheated on Olivia with fellow Disney pop superstar Sabrina Carpenter.
So, join me as I take an in-depth look at just how a diss track battle between Olivia Rodrigo and Sabrina Carpenter took them right off the Disney Channel and straight onto the Grammy’s main stage. Now, this one is a lot. I’m not trying to scare you, but I’m talking about David Dobrik, Jake Paul, Dylan O’Brien, Shawn Mendes, Camila Cabello, Jenna Ortega.
And halfway through this video, the entire story becomes about Sabrina Carpenter. So, grab a snack and get comfortable. But before we get into all of that, I actually want to take a quick break to thank my partner CyberGhost VPN for sponsoring this video. With over 38 million users worldwide and over 20,000 excellent reviews on Trustpilot, it’s one of the best VPNs, period. And you need a VPN.
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So, thank you to CyberGhost so much for partnering with Secret Society, but now back to the video. To really get into the final Disney Channel love triangle and how it launched the two biggest pop stars of current day, I first have to go back to the early 2010s and to Temecula, California, where a 6-year-old Olivia Rodrigo was already beginning her aggressive entrance into the entertainment industry.
Olivia Rodrigo was born to a non-industry family in Temecula, California, but by the time Olivia turned 6 years old, that quickly changed. Even at only 6 years old, Olivia was obsessed with musical theater and was a standout in the small productions put on at her school. Even though her family was primarily made up of therapists and other occupations, they recognized a spark in Olivia that they had never seen in any of their other family members.
So, they enrolled her in acting, dancing, and singing lessons. From then on, Olivia hit the ground running full force. She would finish up her kindergarten classes and be rushed to Los Angeles for constant auditions. These auditions eventually culminated in an 11-year-old Olivia booking the lead role of Grace Thomas. This was for the straight-to-DVD film An American Girl: Grace Stirs Up Success, the American Girl doll of the year for 2015.
And when the movie premiered, Olivia was a complete standout, portraying a young Grace who is tirelessly attempting to save her grandparents’ failing restaurant. And she even ends up landing a spot on the massive TV show MasterChef Junior. I don’t know if this was a huge ad placement or what. Olivia was beginning the audition process for what would be her next big break into the children’s entertainment industry.
And this time it was on the Disney Channel. But by 2011, the golden era of the Disney Channel had come to a close. The network was losing its audience to up-and-coming streaming platforms along with social media. To combat this, Disney Channel and It’s a Laugh Productions Studios launched an intensive writing camp focused on discovering new and young writers, all who were tapped into what kids wanted to watch.
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This is where Disney discovered Kyle Sengita and Josh Lerman. During the intensive writing camp, the two wrote a pilot for a TV show called Paige and Frankie, centered around two tween girls starting a channel on a fictional YouTube platform called Vuugle. Then, after they reached 10,000 subscribers, they moved to Vuugle Studios to start producing their own songs and videos.
The idea was an obvious rip-off of iCarly with a Gen Z twist, industry professionals noting in various trade publications that Disney was capitalizing off of iCarly with a nearly identical format. Madison Hu from Disney Channel’s Best Friends Whenever would screen test with Olivia for the lead roles of Paige and Frankie.
And as soon as Disney executives witnessed their chemistry, they reportedly knew, quote, “They had found their next show.” This was a major deal for Olivia. Sure, she’d starred as the lead role in a movie, but this was the biggest kids network on the planet. And she was being singled out as not just an actress, but a songstress as well.
The show, now titled Bizaardvark, was looking like it had a promising future on the Disney Channel. And Olivia was shaping up to be Disney’s next big star. But there was one huge blight that would shroud the beginnings of Olivia’s career in scandal unlike the Disney Channel had seen since Miley Cyrus.
See, around the time of Bizaardvark’s development, Disney Channel was ramping up to take the competition of YouTube head-on. Children content creators on YouTube were rapidly evolving and way more tapped in than traditional cable networks on what kids actually wanted to watch as they got analytics in real time.
Many of the kids’ channels at the time being parents of young children themselves. To combat this growing multi-billion dollar category, Disney Channel had purchased one of the biggest multi-creator networks on YouTube to hopefully grow their own influential presence on the platform. But their biggest leap of faith was when the Disney Channel signed on growing Vine star at the time, Jake Paul, to star as the lead male role in Bizaardvark.
Jake Paul proudly announced that he was the first influencer to make it on TV, and the press went nuts. News outlets immediately began publishing that Disney Channel had tapped vlog superstar Jake Paul to become their next big thing. Any chemistry Olivia and Madison had on the show would be completely overshadowed by Jake Paul’s physical stunts.
And any interviews meant to build their characters as Disney Channel stars would somehow be just transformed into questions about Jake Paul. Because while Jake was semi-brand friendly when he signed on with Disney, he was also one of the edgier social media stars that they had ever signed on. Fitting him into that Disney Channel mold would prove to be nearly impossible.
This created a weird butterfly effect for Olivia. Because if Jake was never cast, it might have been easier for her chemistry with Madison to take the main stage. But to be honest, Jake is probably the only reason any of us heard about the show to begin with. Other shows like Best Friends Whenever and Andi Mack were failing to make a splash with older audiences like in years past.
And Bizaardvark was taking the strain wreck that was Jake Paul’s social media presence and making it a part of the Disney Channel narrative. The controversy made Bizaardvark the first must-watch Disney Channel had released in years. And when it premiered alongside Sabrina Carpenter’s Disney Channel original movie, Adventures in Babysitting, it seemingly didn’t do as well as Disney Channel thought it would.
As press was largely centered on that movie. But with multiple huge guest stars for the first season, including Logan Paul, the show’s social media promotion was unmatched. Nonetheless, ratings for the show weren’t publicly available beyond a season 3 premiere landing in the top 25 broadcast of the week with 550,000 viewers.
This was a fraction of what shows like Jessie were bringing in every episode. And Jessie was a fraction of what shows like The Suite Life brought in at all. It was clear, the golden age wasn’t just over. Disney Channel’s future wasn’t looking bright, period. And just as season 2 of Bizaardvark had started filming, Jake’s YouTube channel subsequently began blowing up.
And may of 2017, amidst the filming of season 2 of Bizaardvark, Jake released his first rap song, It’s Everyday Bro, actively launching the first content house to the world, Team 10. By the summer, Jake was terrorizing his neighbors and climbing on news vans. It was one of the biggest spectacles in modern YouTube history, and one of the first mainstream crossovers completed by a YouTuber.
The media took this as an opportunity to attempt to squash YouTube the platform entirely. >> >> Headline after headline about how awful of a role model Jake Paul was for young kids began flooding parenting blogs. Disney Channel knew they needed to act quickly, and Jake was seemingly uncontrollable.
Jake later speculated in interviews that Disney Channel hired a full-time surveyor of his content, as he would often get calls reprimanding him for putting the middle finger up in the middle of his videos. Saying Disney was less and less cooperative the more edgy his content got. Thus, in July of 2017, after setting a mattress on fire in his in-ground pool on vlog, Disney Channel and Jake Paul both announced that they had amicably agreed to part ways.
Jake later said that directly after the news coverage of the mattress incident, Disney called him to accelerate the process of removing him from the show. Jake said that was fine, but it looked like Disney Channel had fired him. This is when they both agreed upon the language of parting ways. Now, whether Jake was fired or left this was the first time a main Disney Channel star was completely ousted from a show in the middle of a season.
But it was clear, Jake was a headline machine, one that Disney hadn’t anticipated taking it this far. And Disney saw the warning signs correctly. By the next year, Jake was getting engaged to Tana Mongeau and ramping up the beginning of his boxing career. As the final season of Bizaardvark was filmed, the future of the show seemed really uncertain.
Without the star power of Jake Paul, the show needed a complete overhaul. Disney Channel would controversially move the entire story to take place in a content house, much like Jake’s growing Team 10 house. >> This July, Bizaardvark is changing so much, we had to change the title. >> This is a big deal! >> New stakes.
>> A mansion on the beach where we get to live and make videos all SUMMER LONG. >> NEW SNAKES. [screaming] >> That is weird. >> Same friends. Wait, nope. New friends, too. >> Not candy. Not candy. Not candy. Not candy. I’m not candy. >> The season premiere Bizaardvark, Tuesday, July 24th at 10:30. >> But right before the season premiered, Disney Channel had announced their decision to end Bizaardvark at just over 60 episodes, citing waning viewership.
I don’t know about y’all, but I had no idea Olivia was on the show at all. Obviously, after I started this channel, I knew, but at the time, it did not make a splash for me. While Bizaardvark got Disney Channel viewers acquainted with Olivia, her real namesake breakout role for her music would come in the form of a Disney Channel revival, and subsequently, the meeting of her soon-to-be boyfriend, Joshua Bassett.
2018, the announcement was made at D23 that Disney was bringing back the ultra-popular TV movie property High School Musical, this time as a mockumentary following the students who attend the school High School Musical was filmed at, putting on their own production of High School Musical. This was during the huge reboot revolution of the 2010s and early 2020s, and the meta angle of breaking the fourth wall and addressing High School Musical as an old movie series in the series, let’s just say the stakes were high for a movie
series with such a namesake. When Disney Channel went in to cast the lead male and female characters, just like in movies past, singing was important, but chemistry between the characters was first and foremost. Joshua Bassett was announced as one of the first members of the main cast, and 3 months later, in February of 2019, Olivia was announced as his main love interest.
Now, very little is known about the audition process, but Joshua and Olivia reportedly had multiple chemistry reads together. Joshua’s audition that landed him the lead was his rendition of Bruno Mars’s Count on Me and later his own song that he wrote titled Common Sense. This really highlighted Disney’s desire to cast singers that had mainstream appeal in these main roles.
Ones that could dance, sing, and songwrite. In a 2020 joint interview, Olivia and Joshua revealed that the final audition rounds was a chemistry read and duet together with Bruno Mars’s song Count on Me. Joshua recalled Olivia finding a perfect harmony in minutes, marking them as the strongest actors for the roles.
For the first half of 2019, Joshua and Olivia described the filming process for High School Musical as a magical bubble where the cast got really close. Around this time is when rumors began sparking of Joshua and Olivia dating behind the scenes. Though it’s important to note that neither of them confirmed nor denied the relationship ever existed.
By the time filming for the first season wrapped, it was being reported that the couple were still together but just weren’t seeing each other every day. Joshua and Olivia recorded the duet Just for a Moment for the show. Many fans taking this as a semi-soft launch of their relationship. Nonetheless, High School Musical: The Musical: The Series was a huge show and created just as much coverage, if not more, than Bizaardvark.
The second season of the show was confirmed to have begun filming in February of 2020, but was halted due to the entire world changing for the worse. During this break, the stars of the show would take to social media, posting behind-the-scenes pictures with each other. Olivia and Joshua appearing together the most.
But during this break from High School Musical’s filming is when the story gets really, really messy. See, in June of 2020, budding pop star Sabrina Carpenter was spotted with Joshua Bassett at a protest in Los Angeles. The only problem? Joshua was currently publicly dating his 17-year-old co-star Olivia Rodrigo. >> [screaming] >> Fans on social media immediately began freaking out and jumping to the conclusion that Joshua Bassett had cheated on Olivia.
Olivia didn’t calm the rumors, posting a TikTok with the caption and that’s on failed relationship. Joshua and his team comforted his fans, releasing the song Anyone Else where he sings that he doesn’t want to love anyone else but Olivia. However, over the next few months, Joshua’s budding romance with Sabrina would debut across social media.
The couple was captured going on a lunch date in Studio City with Sabrina’s sister, and they even wore a Sharkboy and Lavagirls couple’s costume for Halloween. Neither Sabrina nor Josh would publicly acknowledge the status of their relationship. And as 2020 came to a close, fans just assumed Joshua and Olivia had moved on.
That is, until January of 2021, when their love triangle would take center stage. On January 8th, Olivia Rodrigo reigned in the final era of Disney Channel beef, when she released her breakthrough debut single Driver’s License. As her voice sang each word, the story became clearer and clearer to fans.
Olivia singing, “I got my driver’s license last week, just like we always talked about. Cuz you were so excited for me to finally drive up to your house. But today, I drove through the suburbs crying, cuz you weren’t around. And you’re probably with that blonde girl who always made me doubt. She’s so much older than me.
She’s everything I’m insecure about. I just can’t imagine how you could be so okay that I’m gone. Glad you didn’t mean what you wrote in that song about me. Cuz you said forever, now I drive alone past your street.” Oh my gosh, I did not hear those words when she was singing it on the radio.
Olivia was very clearly referring to the situation with Joshua and Sabrina. And even though this was very much the retroactive era of championing the women who had been torn to shreds in the early 2000s, Olivia’s young fans absolutely dogpiled onto Sabrina. Sabrina didn’t have the same fan base that the Joshua and Olivia had, so she was at a severe disadvantage.
And honestly, I get pain in my stomach just thinking about being in Sabrina’s shoes at that very moment. Taylor Swift was shouting Driver’s License out for being a beautiful and raw ballad, and immediately gave Olivia critical acclaim that truly can’t be bought. Olivia was four years younger than Sabrina, and had a way cleaner break from Disney Channel, largely avoiding the need for any flop eras, since this was her first single.
Obviously, what makes someone a star is how they handle the really bad situations in the public eye. And Sabrina keeps proving time and time again over this video that she has what it takes to be a massive star. Her Broadway dream had just ended and her new boyfriend came with so much baggage that she had an entire diss track dropped on her.
The world was genuinely closing in hard on Sabrina and she still hadn’t had a breakthrough hit. Her DMs were full of young Olivia stans completely tearing everything she built up for herself to shreds. And while it would be a struggle for anyone to deal with this, Sabrina spun the situation into gold. Because so many eyes were on her as the subject of this hit pop song, record labels were clamoring to sign Sabrina.
Sabrina penned a new record deal with Island Records and immediately hit the recording studio to record what many deemed as her response song. Only 2 weeks later, Sabrina released Skin and she sang the following, “Maybe we could have been friends if I had met you in another life. Maybe then we could pretend there’s no gravity in the words we write. Maybe you didn’t mean it.
Maybe blonde was the only rhyme. Want my heart to be breaking. Though I’m happy that you hate it. Oh, I’m not asking you to let it go, but you’ve been telling me your side, so I’ll be telling mine.” “Oh, you can try to get under my skin while he’s on mine. Yeah, all on my skin.
I wish you knew that even you can’t get under my skin. If I don’t let you in, you’re telling it how you see it. Like truth is whatever you decide, some people will believe it and some people will read between the lines. You’re putting me in the spotlight, but I’ve been under it all my life. I just hope that one day we can both laugh about it when it’s not in our face.
Won’t have to dance around it. Don’t drive yourself insane. I won’t always be this way.” Ooh, drive yourself insane like driver’s license, oof. In an out deleted post, Sabrina insisted she wasn’t bothered by a few lines in the magnificent song that driver’s license was and that Skin is not a diss track aimed at anyone.
She urged people to stop the hate being flung on her behalf or at her saying, “Quote, I don’t condone nor want hate in anyone’s way.” Emphasizing that part of the song speak to multiple experiences, not just one person. However, the lyrics seemed like direct shots at Olivia Rodrigo and Olivia’s fans immediately assumed the worst about Sabrina, labeling her a mean girl and a bully to the younger Olivia Rodrigo.
Joshua Bassett publicly congratulated Sabrina on Skin in an Instagram post, writing that it’d been stuck in his head since he heard it and congrats on her new label deal. Sabrina’s pop career was truly tainted before she even had a chance to break into the pop music industry. She’d been trying music outside of Disney Channel for 4 years at that point and still not seen the mainstream success she had hoped for.
Not only that, now she was being penned as a villain. All before she even had a chance to build her army of fans. But just like her over decade in the industry at this point, Sabrina was persistent, telling Rolling Stone quote, “All I know was that that drama wasn’t going to stop me from doing what I love.
” Now, let’s look at the facts. The narrative of drivers license and Skin painted Sabrina as the evil blonde villain who was stealing a young brunette teen pop star’s boyfriend. Sabrina was labeled as the other woman >> >> and a homewrecker. Sabrina knew how she responded to this clash would affect her career forever.
Thus, she went for the opposite of Olivia Rodrigo’s new and growing aesthetic. She debuted alongside Rihanna in Savage X Fenty Volume 3 and garnered headlines for her shocking new image. And she closed out the year by releasing two singles off her new album titled Skinny Dipping and Fast Times.
It’s important to note that by this time rumors had spread that Sabrina and Joshua quietly drifted apart and even scrapped a duet together on Joshua’s EP. Sabrina clearly wanting to leave the past in the past. However, Joshua Bassett also had some news of his own. After all the public scrutiny and his somewhat lackluster EP release, he would come out as a member of the LGBT community.
Thus, officially ending the blonde girl versus the brunette girl drama entirely. By the end of 2021, it was clear all three of their careers had greatly benefited from the love triangle narrative surrounding them. They were all three bonafide celebrities in their own right. Olivia had broken record after record with drivers license and both her debut album Sour and her sophomore album Guts went number one on the Billboard charts.
She even took home three Grammys for her first album and swept all the newcomer categories. Olivia Rodrigo was a pop rock force to be reckoned with. But what about High School Musical: The Musical: The Series? Even after all of this, Olivia would still return for the show with Joshua like nothing ever happened, continuing press tours for the additional two seasons.
Obviously, Olivia and Joshua were noticeably more distant, and Disney avoided pairing them up for interviews altogether. Clearly, questions about Sabrina or their relationship were off-limits, so the gossip eventually fizzled out even though their relationship was playing out on screen. But, what about Sabrina? She’d been working towards this goal for years, even though it came with some truly traumatizing baggage.
2022 would see the release of Sabrina’s new 13-track album titled Emails I Can’t Send, and it had even more of Sabrina’s perspective on her relationship with Joshua Bassett. Because I Liked a Boy detailed the magnitude of the backlash. Sabrina singing “Now I’m a homewrecker. Now I’m a It’s all because I liked a boy.
” This was definitely a turning point for Sabrina, and sort of the closing of a chapter of the entire drama. It was much better received than Skin, and Sabrina later explained it was her taking her power back and letting people know just how she felt having to respond to all that new backlash. In July of 2022, Sabrina released Nonsense as a single to radio, and it was an immediate hit.
I remember my friend Laura showing me the music video on FaceTime, and I had somewhat lowish expectations before I watched it, but it was an immediate earworm. And the video was so different from anything else at the time. Sabrina was fresh and new, and her image didn’t even completely go with her sound, but she was creating an entire world of a brand, and it would eventually explode on TikTok.
Sabrina would go on the Emails I Can’t Send Tour, playing intimate venues across North America, and they would immediately sell out. And every night, she would change the outro of her song Nonsense, and each would explode on TikTok. Emails I Can’t Send felt like a real coming-of-age album for Sabrina, cementing her with audiences who maybe never even saw Girl Meets World.
Time and Variety magazine noted that Sabrina quietly completed one of the most successful image transitions in recent pop memory, evolving from a Disney princess to a fully fledged pop star through deliberate and steady growth. Sabrina may have had her eyes on the prize, but was reportedly still seen out with Dylan O’Brien in late 2022, but neither of them ever commented on the legitimacy of a relationship.
That was the very niche drama as all the industry was buzzing about was what her 2023 would consist of. She had truly transformed from a niche pop star with an existing audience from her TV show to a clear breakout on the scene. All eyes were on Sabrina. She started the year off debuting on Jimmy Fallon performing nonsense and pumping the song up into her biggest airplay hit yet hitting the pop top 10 charts by February.
In March, Sabrina released her deluxe edition of emails I can’t send featuring feather which immediately soared to number 21 on the Billboard Hot 100 and number one on the United States pop airplay charts. And to her accompanying music video to the single would draw her second major controversy of her career.
When the video for feather dropped in October of 2023, fans were treated to a dark comedy of an avenging angel picking off every awful ex-boyfriend one by one. The video featured each of Sabrina’s exes meeting their cartoonish demise while Sabrina sang about feeling light as a feather.
See, the video was filmed at a Catholic church in Brooklyn and when church officials realized the content, they were horrified. pastor publicly apologized for allowing the video shoot to happen at all. The Bishop of Brooklyn even held a mass of reparation to quote restore the church’s sanctity after the perceived sacrilege.
Sabrina responded telling variety quote, “We got approval in advance and Jesus was a carpenter.” Christians immediately went into outrage. As for the priest who let it happen, the Catholic church was demanding answers saying the normal procedure for filming requires script approval and they didn’t understand how a priest could approve the script.
Messenger Jamie Jean Tello was relieved of his duties and made a public statement apologizing to the Catholic church and its attendees saying he only ever signed off on the project to hopefully strengthen the bonds between the parish and creative artists who make up a large part of this community.
But his apology was to no avail. Each of these stories was building Sabrina into one of the most interesting pop debuts of the early 2020s. Honestly, because of Tik Tok and the decentralization of a lot of the media surrounding music, it was hard in the early 2020s for a pop star to really make a splash. It wasn’t only decided by major labels anymore.
It was widely decided by social media and Sabrina was an expert at that. She knew what to do to get the entire world talking. It wasn’t just her team artificially pumping stories about her. It was the fact that any of those stories were actually newsworthy. Thus, when she was announced as the opener for the greatest tour in modern music history, the world knew where her career was headed.
Sabrina Carpenter would open for pop superstar Taylor Swift on the Eras Tour, a pop music phenomenon unlike the world had ever seen. From 2023 to 2024, Sabrina would serve as the opener on both the Latin American leg and the later Australian leg of the Eras Tour. Stadiums full of tens of thousands of fans would be treated to the musical stylings of Sabrina every single night.
This was without a doubt the biggest moment in Sabrina’s career up until this point. Taylor Swift’s Eras Tour was an online phenomenon. Tens of millions of fans watching live feeds of the concert every night. Taylor even brought Sabrina out for a duet of Espresso and it went absolutely viral.
In addition to the Eras Tour, Sabrina began touring the festival circuit around this time as well. Notably performing at 2023’s Lollapalooza. This is where Sabrina ran into more drama as Page Six ran a story about Sabrina partying with YouTuber David Dobrik. But Sabrina shut it down immediately posting a Lollapalooza dump with the caption, “Sorry, I don’t date Lollapaloozas.
” Complete side note, in 2023, rumors connecting Sabrina to Shawn Mendes would go everywhere. They were allegedly seen on a few dates back in February of the same year and seen leaving Miley Cyrus’s album release party in March. Entertainment Weekly even ran a story that they were seeing each other. However, Shawn would go on Dutch TV and insist he and Sabrina were not dating and then briefly be seen with his ex fellow pop star Camila Cabello.
>> We are not dating, but I think we should talk about Tommy Hilfiger probably more than Sabrina, but thank you. >> Being with someone two days before seeing your ex and communicating two days before that that you’re going to go hang out with your ex? >> Camila even wrote lyrics alluding to her weekend with Shawn at the music festival in her track June Gloom.
>> I come in like a coach out >> >> That’s when Sabrina later released her songs titled Coincidence and Taste. Fans connected some of the lyrics to Shawn as a guy who’s still hung up on one of his old exes. Taste was actually wild. Sabrina singing, “I heard you’re back together and if that’s true, you’ll just have to taste me when he’s kissing you.
If you want forever and I bet you do, just know you’ll taste me, too.” Sabrina would even shoot a music video for Taste where she would cast Jenna Ortega. Many seeing this as a direct look-alike for Camila. She would close out 2023 as the major new pop culture icon to look out for.
Announcing her new tour titled Short and Sweet for 2024 and it sold out in minutes. She would also be spotted with a new character in her life, Barry Keoghan, in December of 2023. And by early 2024, Sabrina hard launched the relationship at the Vanity Fair Oscar party. In March, Sabrina began teasing her new era.
But little did anyone know that over a decade of hard work Sabrina Carpenter had put in at this point had perfectly primed her for what would be the biggest moment of her career. Shattering any doubts anyone had about Sabrina’s longevity and growing her into a true force to be reckoned with. On April 11th, Sabrina released the first single off her new album and it was called Espresso.
The next day, Sabrina would perform a high-energy rendition of the song at Coachella day one and within days, it shot to the number one spot on Spotify’s charts. And by the end of Coachella weekend, Espresso was trending number one worldwide on Twitter and TikTok. Over the summer, Espresso only grew, reaching number one in dozens of countries and by the end of the year, it became the most streamed song on Spotify in 2024 with 1.
6 billion streams. Sabrina even got her first VMA win for a song of the year. If there were any doubts about Espresso being a fluke, all those worries quickly subsided when Sabrina’s follow-up single, Please Please Please, made up chart history. The song debuting at number one on the overall Billboard charts.
Sabrina miraculously held the number one and two positions on the UK charts for several weeks, making her the first artist in UK to hold both top positions for over 3 weeks. By midsummer 2024, Sabrina had accomplished what many had written off as impossible for her. She was on every magazine, at every event, and blasting across every radio.
In August, Sabrina released her highly anticipated album Short n’ Sweet, debuting at number one on the Billboard charts and selling 362,000 units in its first week, one of the biggest openings of the year. Sabrina managed to do something not seen since the Beatles. Her first three singles, Espresso, Please, Please, Please, and Taste, all ranked in the top five of the Hot 100 simultaneously.
They remained in the top 10 together for 7 weeks straight, a new record for a female artist. This is when her entire narrative became what it’s known as currently, and most likely will be for a long time. People stopped comparing her to the likes of her Disney Channel peers. They began comparing Sabrina to pop titans like Ariana Grande, Dua Lipa, and of course, Miley Cyrus and Selena Gomez.
Amid all of Sabrina’s appearances like Christina Aguilera’s 25th anniversary special and her own Christmas special with Shania Twain, she would also go on her first sold-out arena tour. It was a massive moment for Sabrina. Her album was breathing new life into the pop industry. As V Magazine said, Sabrina’s career has matured faster than any of her Disney bred predecessors, evolving into a confident pop act with a distinctive point of view.
However, by 2024’s end, multiple outlets began reporting that Sabrina split from her boyfriend Barry Keoghan and was now single. Her career was coming first. 2025 Grammy nominations reflected all the work Sabrina had been putting in, claiming nominations for Best Pop Solo Performance and Record of the Year with Espresso, Song of the Year with Please, Please, Please, Best Pop Vocal Album, and most ironically, Best New Artist, even though she’d been releasing albums for almost 11 years at that point.
Sabrina took home the Grammy for her album Short n’ Sweet and Best Pop Solo Performance for Espresso. In her emotional speech, Sabrina acknowledged every single one of those 12,000 fans who bought her debut album. >> I feel so lucky to be able to come together and and do something so special and beautiful and celebrate music.
Um, I want to thank all the fans that let my music be heard by the Recording Academy. I want to thank my mom for driving me to every voice lesson in Balaklava. And I want to thank my dad and my sisters. I want to thank my team. Thank you. This is so special to me and short and sweet means the world. >> In a real full circle moment, Sabrina was spotted talking to none other than Olivia Rodrigo at the ceremony, officially putting any rumors of a bitter rivalry to rest.
Even telling the press she genuinely doesn’t think about it ever. And it’s clear she doesn’t even really have time to think about it. Sabrina has become a massive celebrity, but she’s someone who has been true to herself. Even watching her old Disney Channel interviews and scenes, yes, she’s a tomboyish Sam Puckett character, but she’s still that bubbly blonde that’s shocking the world with her new Juno position every week.
Of course, Sabrina’s drawn the same criticism plaguing Disney Channel stars for years. Miley Cyrus genuinely shattering that ceiling with a wrecking ball, the way has been so thoroughly paved that a lot of her criticisms almost just feel like PR strategy on the part of Sabrina’s team. Just to make her seem more subversive than she really is.
Sabrina Carpenter is a complete new take on the modern pop star. And it’s clear she isn’t going anywhere anytime soon. Anyway, that’s really all I have for this video. So be sure to subscribe if you liked it. Comment below what you think and thank you so much again to CyberGhost VPN for partnering with me on this video.
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>> Got a whole personality [music and singing] that knows >> [cheering] >> the song is not about Joshua or anyone >> [screaming]
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