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In honor of the LP’s Sweet 16 anniversary, iHeartRadio decided to take a walk down memory lane, grab a copy of the CD and revisit the blockbuster album. We sifted through old interviews, spoke with collaborators and even took a glance at the album booklet. You know, the paper pages inside the jewel case that you used to read. Take a look below!

Not only did Max Martin produce a majority of the songs on Oops, but he also voiced that geeky astronaut that pops up mid-way on the title track. Cue your “Britney, before you go, there’s something I want you to have” imitation.

Years before her 2004 cover of “My Prerogative” off her first greatest hits compilation, Britney (or at least her 2000 album sessions) crossed paths with R&B singer Bobby Brown. If you take a look at the production credits, you’ll notice that Bobby is credited as one of the assistant recording engineers on the project.

There’s a batch of famed songwriting credits on the LP, including Shania Twain and her then-husband/producer Robert “Mutt” Lange (“Don’t Let Me Be The Last To Know”),Diane Warren (“When Your Eyes Say It”) and even Britney herself (“Dear Diary” was her very first foray into the writing game). Mick Jagger and Keith Richards also make appearances, courtesy of Darkchild‘s makeover of The Rolling Stones‘ “(I Can’t Get No) Satisfaction.”

Even though her cover of “Satisfaction” was mostly panned by critics, the song was a glimpse of Britney’s authoritative nature. As the story goes, B used to listen to the 1965 classic with her girlfriends when she was younger, so she approached her record label to cover the song. After they shut down the idea, she went ahead and recorded the song anyway. Look at Rebellioney making an appearance back in 2000.

There’s also another cover song on Oops. Well, that’s if you own one of the various imports of the LP. Britney’s cover of The Jets‘ 1986 “You Got It All” from her …Baby One More Time sessions is included as a bonus cut on alternate import editions of the album.

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Photo: Wendy George for iHeartRadio

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Photo: Getty Images

Jason Blume, the co-writer of “Dear Diary,” told iHeartRadio that the original ending of the song involved a guy cheating on her, but the label didn’t like that kind of outro, so he wrote six alternative endings and ended up meeting with Britney to work on lyrics for an idea she had to offer.

No one really knows when Britney and Justin officially became a thing, but Blume admitted that JT was actually in the studio during the recording of “Dear Diary.” “You don’t fly yourself to another city with somebody unless you’re pretty involved,” he explained of the then rumored couple. “It was obvious. She just lit up when he walked in the room.”

Britney was not a fan of her 15-year-old self on the cover of …Baby One More Time. In fact, she “hated” the girly shot so much that she made sure that she had a say in the cover for Oops. Even though she initially wanted legendary photographer Herb Ritts to shoot the album campaign, she ended up with Jon Ragel for the beaded curtain shot.

Britney recorded half of the album in just one week.  During her 2000 Rolling Stone cover story, she acknowledged that the process was rushed. “The new album is really hot, but I just know how much better it could be,” she said. “I think about the third album, and I’m so excited because I know I’ll be able to have, like, six months. I want to be able to be in the studio 24/7 and just do my thing. I won’t be having to do the commercials and all that. I’ll just be motivated by one thing.”

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Does Britney prefer “…Baby One More Time” or “Oops!… I Did It Again”? Back in 2000, she chose the latter, admitting that the future pop anthem was better than her debut single.

Even though Britney only had one writing credit on the LP, she still had a lot of say in vocal production. Album collaborator Barry Eastmond told iHeartRadio that she “tried a lot of different melody ideas” during album sessions. “Britney does some melodic riffs that show her upper range as well. I was very impressed at how hard she worked on these vocals. I think we worked six hours one day and then she came back the next day and sang for another three hours,” he said of his work on “Dear Diary.”

Oh, and in case you weren’t aware, Oops!… I Did It Again held the title for the biggest first week sales for a female artist in the United States for 15 years. It sold a whopping 1,319,000 copies in the first seven days of release and was only dethroned last year by Adele‘s massive selling 25, which moved 3.38 million copies.

B used to make up melodies in her head and jot down journey entries or leave voice memos for her producers. “The more and more I did it, the better I got,” she said of the melody creations.

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Let’s celebrate the Oops anniversary with some cupcakes!

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Photo: Wendy George for iHeartRadio

Make sure to watch Oops on Vevo! Let’s get OopsNey Vevo certified ASAP!

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