Ariana Grande Walked Us Through Her "Crazy" Beauty Evolution

"This is about to be crazy," Ariana Grande tells her entourage when she learns what we have planned for our sit-down interview. "This is going to be pure comedy — I’m terrified!"

To celebrate the launch of the 23-year-old's latest fragrance, Sweet Like Candy — a scent she describes as "a younger, sweeter, more flirtatious version of the Ari fragrance" — we decided to take a look back at the singer in her younger days. We arrived at Ulta Beauty, the store that launched the scent exclusively, armed with 12 photos of Grande's most striking looks and asked her to comment on each. Which does she still love? Which does she hate? You'll find out ahead — along with a lot of discussion about that ever-present ponytail.

"I'm not sick of talking about it...I know it's a thing," Grande says when asked if she's hit peak pony-talk. Probe a little further and you'll learn that her signature style has become a blessing and a curse — which is why it made it into her latest release, "Jason's Song," with industry veteran Jason Robert Brown. The lyrics read: "You acted like you bought me at a bargain sale / You don't even care / You focused your frustration on a small detail / Blew it out of scale, like my ponytail."

"I remember sitting with Jason in my studio saying 'I love music so much, but I wish that's what people saw first and foremost,'" she told us. "Jason knows me as a singer, as a musician, as a person he cast on Broadway, so his response was, 'What the hell are you talking about?' And I was like, 'My ponytail!' He was like, 'Is that a thing?'" A "thing" it is, indeed, and calling it out is just one part of why the song is so special to her, she says.

In case you're wondering: Yes, she was wearing her go-to half-pony for our interview, the same one she's sporting in most of the shots that get published, but click through and you'll see in the star's evolution that's she's far from a one-hit wonder.

This story was originally published on September 29, 2016.

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Photo: Joe Corrigan/Getty Images.
New York City, 2008

"Look at that little nerd! [Laughs] Whoa, dude, look at that! I look like a little baby. My first response is whoa. It’s fine because, like, that’s me. That girl is tight — she was on Broadway! I embrace every phase and I love every step of that way, but that look is wild. But I was also 14 years old. That is the height of my awkward phase — that was the peak."
Photo: Jesse Grant/WireImage.
Los Angeles Premiere Of Fantastic Mr. Fox, 2009

"Cutie! That was my first red carpet! I remember being so calm and not really knowing what the hell was happening, but having a great time, Also, I was thinking, ‘Why am I here?’ I wasn’t even in that film! [Laughs] I guess they were like, ‘Oh, she should go to this event just to try it out.’ I feel like I was much better at walking the red carpet then, compared to now. Look at that: calm, cool, and collected!

"This hair I had dyed for Victorious. This was season 1 Cat Valentine hair — it was kind of shorter and brighter, and as the show went on, it got a little longer and a little darker. I look like a little baby. The red wasn’t a pain to remove as much as it was to keep up for such a long time — I paid the price for a little while, but my hair is super healthy now.

"I kept it for the first four years of working on the show, then we switched to a wig later on. Towards the last season of Sam & Cat, there was too much back-and-forth between [my] music and the filming to keep dying it. We had this great wig made, and it made everything a lot easier — and my hair healed!"
Photo: Kevin Mazur/WireImage.
MTV Video Music Awards, 2013

"Awww I like this one! This was the floral-dress-and-side-bang phase. See? The ponytail has had quite the evolution — not to toot my own horn. I do love the ponytail, but there are many different ways to execute the ponytail. The pony was sort of off to the side — by accident I think. See, that was a nervous tick, to twirl and pull it off to one side.

"The ponytail has always been a part of my life. I started doing the ponytail in middle school when my friend Suzanne and I always had these crazy, floppy side-ponytails, but I do like to mix it up now and again."
Photo: Steve Granitz/WireImage.
MTV Video Music Awards, 2014

"Whoa! It's crazy going from that [previous picture] to this. Pretty sure I was very anxious when this photo was taken — I was like, 'VMAs!' We did the 'Bang Bang' lip color, which was the Magenta M.A.C. lip liner — how do I remember that?"
Photo: Venturelli/WireImage.
MTV European Music Awards, 2014

"Yeaaah. A lot going on here. I think there is some powder in my eyebrows? Ahem. Not my fave and I will leave it at that."
Photo: Larry Busacca/Getty Images.
Grammy Awards, 2015

"I did that makeup myself and my mom styled me! This is one of my favorite things I have ever worn on the carpet — this Versace. I was having a lot of trouble finding a dress and everyone was really stressed because the stakes were high because I was performing and nominated. It was a big day for me and, literally, my mom called Versace and was like ‘My daughter needs a dress! Can I come in and pick a dress?’ My mom hooked it up.

"I am obsessed with the Anastasia highlighting palettes — they are everything. My nose looks like the New Year's ball — it’s hilarious."
Photo: Allen Berezovsky/WireImage.
Los Angeles, 2015

"YAS! This was one fun! I love the bronze-y colors on the lid — thank you Daniel [Chinchilla]! I love that champagne-pink, yummy, warm lid. The red lip is tight. This attitude on the hips is crazy. The half topknot is kind of cool; it still accomplishes the hair out of the face, which is very important to me — I like to keep it up or back. I get too fidgety. I am not used to it being down."
Photo: Neil P. Mockford/GC Images.
London, 2015

"I look very nervous here! I am a big fan of space buns and these are cute! I like my rain coat — that was a really fun outfit.[Monochromatic lips and eyes] is definitely my go-to.

"I have so many '90s icons — my musical and beauty and style icons kind of go hand in hand. A lot of the ‘90s music that has influenced me has also influenced my style lately."
Photo: Kevin Winter/Getty Images.
American Music Awards, 2015 (Performance)

"I had to do a quick change into a topknot bun for the audience look, so we did this wig [for the performance]. I had a 102-degree fever when I did this performance, so that’s all I see what I look at that this — chills!

"I would dye my hair this dark when I feel like switching it up next. Color is definitely something that I would play with, but in general, my favorite is being more of a blond-y color with ashy tones. I like my Lola Bunny hair I have now. So, after the ['describe yourself in three fictional characters'] Facebook challenge, I have decided that I am Lola Bunny from Space Jam. There's no option; that’s me."
Photo: Steve Granitz/WireImage.
American Music Awards, 2015 (Red Carpet)

"I do a lot of topknots in my off-time — different fun looks — but this was the red carpet, super-done-up version of it. I think I like the casual one more than this, but it was a really fun look because there was a lot of detail; it’s like a fishtail-y top knot.

"[The secret to a good cat-eye?] You say a little prayer and you try a bunch of times and then eventually, once you’ve run out of eyeliner three times, you get it right. [Laughs] Everyone has their own strategy, but I just kind of hope for the best. I use a liquid liner but [my makeup artist] Daniel uses a pot with a brush and he’s much better than me."
Photo: Kevin Mazur/Getty Images.
New York City, 2016

"I like these [braids]; this is cool! I was promoting Dangerous Woman, going around saying, 'I hope you like it' to everyone. [Laughs]"
Photo: Jeff Kravitz/FilmMagic.
MTV Video Music Awards, 2016

"This was my favorite hair and makeup look — and outfit — on the carpet. H to T, this was my favorite carpet look ever. I am crazy about the crimp texture, I think that is is such a cool thing to do.

"Also Aaron [Light] chopping my bangs. We tried some clip-ins for the 'Side To Side' video together and they completed the picture. Two days after we shot that video, I was like, 'We have to cut these!' I love them. I can do heavier bangs with all the pieces forward, for more of a ‘60s Brigitte Bardot, or I can pull some back and have these little cuties."
Inspired by Grande's epic beauty evolution, we decided to recreate three of her signature looks. Press play to see this transformation unfold, turning one Ariana fan-girl into a pop star look-a-like.
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