Honestly, it feels like a lifetime ago when Ariana Grande was rocking that high ponytail for the first time and Big Sean was the undisputed king of G.O.O.D. Music. But if you turn on a 2010s R&B playlist today, their collaborations still hit different. People always talk about their relationship—the Coachella hand-holding, the "thank u, next" shoutout—but the music they made together actually shifted the trajectory of both their careers.
It wasn't just a PR stunt.
They had this specific sonic energy that was part 90s throwback and part modern hip-hop swagger. Every Big Sean and Ariana Grande song felt like a chapter in a very public, very melodious diary. From the honeymoon phase to the messy "researching your ex" phase, they put it all on wax.
The First Spark: Right There
Before they were an "it" couple, they were just two artists trying to find the right vibe. Back in 2013, Ariana was transitioning from Nickelodeon star to a serious vocal powerhouse. She was looking for a sound that felt more "Mariah" and less "Cat Valentine."
She found it with "Right There."
Basically, Ariana had been sitting on the track for a while. It samples "Rain Dance" by The Jeff Lorber Fusion—the same beat Lil’ Kim used for "Crush on You." It’s got that heavy snare and those 90s snaps. Ariana mentioned in interviews at the time that she and Sean had been friends for a minute, but they couldn't find the right track to jump on together.
When "Right There" finally clicked, it became the "sequel" to her breakout hit "The Way." Sean’s verse? It’s classic Detroit Sean—witty, a little bit cocky, and full of double entendres. He recorded his part in Paris, while she was in L.A. Even though they weren't in the same room, the chemistry was undeniable.
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The music video took things to another level. It was a 1920s-meets-Romeo-and-Juliet masquerade ball at a mansion in Beverly Hills. Sean played the priest/narrator role. Looking back, the religious imagery and the way he looked at her on set was the first real clue for fans that something was brewing off-camera.
The Peak: Best Mistake and the Relationship Rumors
By the time "Best Mistake" dropped in August 2014, the world was obsessed. They had been spotted together everywhere. This song didn't just hint at a relationship; it basically confirmed they were dealing with some heavy, real-world emotions.
Unlike the upbeat tempo of their first collab, "Best Mistake" is a moody, piano-driven ballad. It’s stripped back. Raw. Key Wane produced it, and he left enough space for Ariana’s lower register to actually breathe.
"You're the best mistake I've ever made / But we hold on, hold on."
The lyrics are surprisingly mature for where they were in their careers. Sean raps about "ziplocking" feelings to keep them fresh and mentions Ariana's mother, Joan, saying he loves her because she's an "older version" of Ari. That’s not a generic rap verse; that’s a love letter.
It was a massive commercial success too. Ariana became the first artist since Michael Jackson to have three songs in the top ten of the Billboard Digital Songs chart simultaneously, and "Best Mistake" was a huge part of that. They performed it live at the iHeartRadio Theater and "A Very Grammy Christmas," and you could practically feel the tension through the screen.
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The Turning Point: Research and the End of an Era
If "Best Mistake" was the honeymoon, "Research" was the fallout. Released on Sean’s Dark Sky Paradise album in early 2015, this track took a sharp turn into the "toxic" side of romance.
The song is about a suspicious lover who is essentially acting like a private investigator—checking DMs, looking at "G-mails even P.O. boxes." It’s a bit of a weird listen because Ariana provides the hook, validating Sean's complaints about a "crazy" ex. At the time, everyone assumed the lyrics were a direct shot at Sean's ex-fiancée, Naya Rivera.
It was bold. It was kind of messy.
Critics were split. Some loved the Metro Boomin and DJ Dahi production, while others felt the lyrics were a bit harsh. But that’s the thing about a Big Sean and Ariana Grande song—they never played it safe. They were willing to put the uncomfortable parts of their lives into the music.
Shortly after "Research" made its rounds, the couple officially split in April 2015. They cited "conflicting touring schedules," but the music they left behind told a much more complicated story.
Why These Collaborations Still Matter in 2026
You might wonder why we’re still talking about songs from over a decade ago. It’s because these tracks represent a specific era of "Pop-R&B" that has become a blueprint for artists today.
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- Genre Blending: They proved that a pop princess and a "rapper's rapper" could create something that didn't feel forced.
- Vulnerability: They used their real-life drama to fuel their art, which created a deeper connection with their fans.
- Visual Storytelling: Their videos weren't just clips; they were cinematic events that defined the aesthetic of the early 2010s.
Even years later, when Ariana released "thank u, next," she wrote "so cute, so sweet (could still get it)" next to Sean's name in her "Burn Book." They’ve remained friends, and they were even spotted together at a recording studio in 2019, though a new song never materialized from that session.
Actionable Insights for Music Fans
If you're looking to dive back into their discography or just want to appreciate the technical side of their work, here’s how to do it:
- Listen to the Unreleased Versions: There are solo demos of "Right There" and "Best Mistake" floating around. Comparing the solo versions to the final features shows exactly how Sean's verses changed the dynamic of the tracks.
- Watch the Live Performances: Specifically, find the Detroit stop of The Honeymoon Tour. The energy in Sean's hometown while they performed together is something you can't get from the studio recording.
- Study the Samples: Check out "Rain Dance" by Jeff Lorber. Understanding the jazz roots of "Right There" gives you a much deeper appreciation for the production quality Ariana was aiming for early on.
The legacy of the Big Sean and Ariana Grande song catalog isn't just about a celebrity couple. It’s about a specific moment in time where hip-hop and pop collided in a way that felt authentic, messy, and perfectly harmonious.
To fully appreciate the evolution of modern R&B, go back and listen to My Everything and Dark Sky Paradise back-to-back. Focus on the production shifts between "Best Mistake" and "Research." Notice how the instrumentation moves from organic piano to aggressive, trap-influenced synths. This transition mirrored the shift in the music industry at large during the mid-2010s, proving that Sean and Ariana weren't just following trends—they were setting them.
Check your favorite streaming platform for the "Complete Ariana & Sean" playlists created by fans; they often include the remix of "Problem" and other deep cuts that didn't make the radio but defined the era.