Diddy signs a young singer with a hit single who’s on the fast track to fame. Cassie Ventura reportedly agrees to a 10 album deal. They become romantically involved and Cassie’s career flatlines, leaving fans wondering why she only released one studio album. We chart their decade-long relationship -- from the glamorous red carpet appearances to allegations of hidden abuse. A warning that this episode includes discussion of sexual violence and abuse. If you or someone you know is a victim of domestic violence, please call the domestic violence hotline at: 1-800-942-6906 or go to https://www.thehotline.org. Learn more about your ad choices. Visit podcastchoices.com/adchoices
Chapter 1: What is the main topic of this episode?
A warning, this episode includes discussion of sexual violence and abuse, so please take care when listening. In 2006, more than a dozen people sat around a long conference table scattered with water bottles and shiny folders emblazoned with a bad boy logo.
This was the era of flip phones and DVDs, so people glanced at paper handouts inside their folders as they scribbled down notes in actual notebooks. Sean Diddy Combs had gathered everyone to tell them about a new artist he'd signed to his Bad Boy Records label.
Diddy was in the middle of a successful run with Danny Kane on his MTV show Making the Band, and he was getting ready to release the debut album of Atlanta rapper Young Jock. But Diddy wasn't happy with the label's recent performance. He said publicly that he was trying to get things back on track. So now he had another up-and-coming artist he wanted everyone in the room to meet. Cassie Ventura.
That day, she wore her long, dark hair tucked behind her ears and big gold hoop earrings. She dressed casually, with little to no makeup. Combs was in his late 30s. He sat at the head of the conference table while 19-year-old Cassie was at the other end. She was there with a producer she'd been working with. They'd released a song you've probably heard of called Me and You.
To this day, Me and You is the track Cassie is best known for. A song that would go on to peak at number three on the Billboard Hot 100. A song that stayed on the charts for about six months. In other words, back in 2006, Cassie's song was one of the country's most popular singles.
It's an infectious song. It has a weird, creepy vibe, but at the same time, it's fun to sing along to, and it's just simple.
For me, this song brings back memories of being 18 years old and driving around with my friends in my mom's car. It was the kind of song where if you heard it on the radio, you'd tell your friends, yo, turn that up. It was this song that caught Diddy's attention.
He told everyone gathered at the conference table that the song had been haunting him in nightclubs and that he thought Cassie had a personality that, quote, the whole world could fall in love with. Before Bad Boy released a remix, Me and You was already an underground hit, even without the backing of a big record label. Cassie Ventura had built up a fan base DIY style.
The secret ingredient was early social media. Remember Myspace? Myspace was only about three years old at the time. It was the beginning of social media for millennials like me who grew up in the 90s and early 2000s. My profile had posts about soccer players I liked, like Ronaldinho, Zizou, and Henri, and some of my favorite music.
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Chapter 2: How did Cassie Ventura start her music career?
Put your hands together for the Princess of Next Collection. Make some noise. Cassie, come on.
What's up, E.T.?
What? What? What?
At one point, the camera pulls back to show the crowd, and there's only a few people dancing. The whole thing feels very low energy.
Cassie had one of the most disastrous performances we've seen on live television, on 106 and Park.
Jamila Lemieux is a writer and cultural critic. She remembers Cassie's BET debut.
And this was very early into her career, just, you know, within months of her debut single, Me and You, coming out. And Diddy takes to the Internet to defend her very passionately, you know, in a way that didn't seem to line up with who he had been, say, on making the band and having these very high, rigorous standards for performance.
Some fans didn't think Cassie met those high standards for Bad Boy. I found an online petition to get Cassie kicked off the label that referenced both this BET performance and another one on MTV. The petition got over 3,000 signatures, so not tons considering she had hundreds of thousands of followers on MySpace, but still, it was pretty vicious.
The petition was titled, We Prefer Lassie Over Cassie, and whoever started it complained of Cassie's penguin-moaning vocals. But after the BET performance, Diddy seemed to stand by Cassie. He told MTV, It just made me appreciate that she got nervous, and it was kind of cute to me, to be honest. He said he told her, It's like riding a bike. You're gonna fall down. You gotta keep on getting on it.
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Chapter 3: What was Cassie's breakthrough hit and its impact?
Now let me ask you this, did Cassie object at all to any of the nudity or she was totally cool with it? Cassie, she's from Europe. Yeah, so she's open. No, no, it's not that. It's just like when you've been a model and you're doing it for the art, it really wasn't done for the commerce. It was done more for the art side of it.
Side note, Cassie's not from Europe. She grew up in Connecticut. Anyways, what stands out to me here is that Cassie, the recording artist, she's no longer in the frame. It's like she's become more of an accessory, an extension of Combs and his brand. In 2015, Bad Boy Records celebrated its 20th anniversary. The next year, Diddy organized a 24-city family reunion tour to celebrate.
He was the headliner, and he invited legacy bad boy artists like Lil' Kim, Mase, and Faith Evans to share the stage. Some of the shows included special guest appearances from artists like Jay-Z, Usher, Snoop Dogg, and Mary J. Blige. Cassie performed at some of these concerts, but she wasn't a headliner, and she doesn't show up in the press release. And if you look for her, you can find her.
She's there, at least at some of the shows. But she's not out front and she's not being promoted. She's clearly part of the supporting cast. So maybe that makes sense. After all, she hasn't had another hit song in 10 years. She's sort of a one-hit wonder at this point. At least that's one interpretation. But maybe she's not out front because she's being stifled.
People like DJ and culture critic Megan Wright began to wonder if Cassie's career was being held back intentionally.
I think being in the music industry, you would hear these rumors and then you have these questions about whether or not Diddy was controlling Cassie and whether or not he was controlling her music. Because you look at her debut in 2006 and then her music career after that, you know, nothing that she did really hit Cassie.
the same marks as they do in 2006, which is common and can happen to other artists, but we began to see her more in the public as Diddy's girlfriend and less as the artist Cassie.
But she was still recording music. Back in 2012, an anonymous fan posted 66 unreleased Cassie tracks on a social media site called Tumblr that was popular at the time. It isn't clear how the fan got these songs or why some of them had never been released by Bad Boy. The collection was titled The Cassie Trilogy.
And if you search around the internet, you can still find a link with all of the leaked recordings, including this track titled Sound of Love. We don't know if this collection of leaked songs put pressure on Bad Boy, but a year later, in 2013, the label released a Cassie mixtape called Rockabye Baby. A mixtape isn't the same as a commercial studio album.
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Chapter 4: How did social media play a role in Cassie's early success?
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