When the annual awards show kicks off live from Radio City Music Hall in New York City on Monday, the 49-year-old singer will return to the stage for her first VMAs performance since 2001. Additionally, she'll also be taking home the most prestigious prize of the night, the Michael Jackson Video Vanguard Award.
Ahead of the show, ET's rounded up Lopez's best music videos from her 20 remarkable years in the spotlight. Check them out below!
1999: "Waiting for Tonight"
Although "If You Had My Love" from her debut studio album, On the 6, was technically her first-ever music video, Lopez credits this one as being a big first for her in many ways. "It was the first time I went into the editing room and sat side by side with the editor, Dustin," she recalled in a recent Instagram post. "That's when I realized the magic of editing. Since then, I've been involved in the editing of all my videos."
"'Waiting for Tonight' is one of my all-time favorites because it stands the test of time," she added. "It was 1999, just about to be 2000 or Y2K -- everyone thought the world was going to crash, so the director, Francis Lawrence, and I just threw the ultimate rave in a rainforest!!"
The video scored her the best Dance Video award at the 2000 VMAs.
2001: I'm Real (Murder Remix)" feat. Ja Rule
This was the video that made nearly every young girl in the early '00s splurge on -- and later regret buying -- a velour sweat suit from Juicy Couture, oversized hoop earrings and white Adidas sneaks in hopes of "poppin', hoppin'" around in clothes that resembled the Bronx, New York, native's sporty-chic style.
"We shot [the video] in one day," J. Lo explained via Instagram. "The stylists brought me all this fancy couture from all the big designers. But this little known company Juicy sent these sweatsuits for me to chill and hang out in ... I shocked everyone when I decided to wear it! It seemed fitting since the song is called 'I'm Real,' so I decided to be ME!"
Featuring Ja Rule, the song was part of the 2002 reissue of Lopez's second studio album, J.Lo, which was titled J to tha L-O! The Remixes. The two performed the hit track at the 2001 MTV Video Music Awards, which is surprisingly the last time fans saw Lopez hit the VMAs stage. Luckily, that all changes on Monday, and we can only hope Lopez includes "I'm Real" in the medley of songs she's preparing for the highly anticipated show.
Hoping to feel real nostalgic? Who remembers this space-themed, computer generated music video? We have to admit... we almost forgot this one even existed, but after taking a trip down J.Lo memory lane, we couldn't help ourselves from including this masterpiece. Gauchos (remember those?), knee-high boots and curly hair? It's perfect.
2001: "Ain't It Funny" (Murder Remix)
Lopez teamed up with Ja Rule once again for a remix of her third single from On the 6, "Ain't It Funny," which also featured vocals from Caddillac Tah and Ashanti. While there's not as much dancing as usual from the brunette beauty, it's a delightful throwback, nonetheless.
2002: "I'm Glad"
Directed by David LaChapelle, the Flashdance-inspired video was considered one of the "sexiest" music videos ever made at the time. Lopez played homage to the 1983 film by sporting a variety of bodysuits, off-the-shoulder sweatshirts and sultry stage costumes that perfectly resembled the iconic pieces worn by Jennifer Beals. Plus, the choreography was so spot-on, that only someone like J.Lo could pull off those moves so flawlessly!
2002: "Jenny From the Block"
"Don't be fooled by the rocks that I got. I'm still, I'm still Jenny from the block." Nearly 16 years after its release, this classic song (and its accompanying music video) from her third studio album, This Is Me... Then, is arguably one of Lopez's most popular pieces of work to this day.
If you haven't seen this video since its initial debut, you're in for a real treat -- rewatch it above to see a 33-year-old J.Lo show off her enviable abs in a bright pink bikini, along with footage of her with her former fiancé,Ben Affleck, prior to their split in 2004.
2003: "Love Don't Cost a Thing"
Classic J.Lo! Shot in Miami, Florida, Lopez pulled out all the stops for this video, keeping it fresh in a white crop top emblazoned with her name in rhinestones, along with cornrows and her signature hoop earrings for her epic dance break starting at the 2:44 mark. Footage from the set was featured on MTV's Making the Video and the video was a constant play on TRL at the time.
2005: "Get Right"
At the 2005 MTV Video Music Awards, Lopez received four nominations for this video -- Best Choreography, Best Electronic Dance Music Video, Best Direction and Best Editing. Though she unfortunately didn't take home any wins, this video (and her impressive choreography!) will forever go down in history. Rewatch the video above and see if you can keep track of all the different characters the triple-threat portrays.
2011: "I'm Into You" feat. Lil Wayne
From her bombshell beach hair, to the enviable outfits, to the flirty scenes with a sexy shirtless man, it would be a crime not to include this video on the list. Oh, and who could forget that fiery dance number starting at the 2:58 mark? It's a must-see!
2011: "On the Floor" feat. Pitbull
One of Lopez's most popular of all time, the music video for "On the Floor," off her seventh studio album, Love?, has surpassed 1.2 billion views on YouTube.
"This was my first track after I had my babies," Lopez, who shares 10-year-old twins Emme and Maximilian with ex-husband Marc Anthony, said in a recent Instagram post. "I hadn’t put out a record in a few years. They gave us no money to make this video."
"It ended up leaking a few days before my debut on American Idol, and started climbing straight up the charts!" she continued. "It’s also my first video to reach one billion views on YouTube, and I was the first female artist to do that."
2012: "Goin' In" feat. Flo Rida
Bedazzled lips, rhinestone crop tops, wolves, breakdancing and hydraulics -- what more could you possibly want out of a music video? The catchy song was featured on the soundtrack for Step Up Revolution, which starred her future The Boy Next Door co-star, Ryan Guzman.
2014: "Booty" feat. Iggy Azalea
If you've got it, flaunt it, right? These bootylicious babes put their best assets on display in the music video for the third single off Lopez's eighth studio album, A.K.A. Dressed in a high cut, black bodysuit, Lopez left very little to the imagination, twerking and going "to werk" around the music video set with Azalea.
2018: "El Anillo"
Proving she's not going anywhere anytime soon, the pop queen surprised us with yet another fab music video in April, for her latest Spanish-language single, "El Anillo," which translates to "The Ring."
"There's just a special excitement. The song is a great song. It's a fun song, it's a surprising song," Lopez explained to ET when we exclusively visited her on set. "It's really about recognizing your own value. That's where women are right now, and all of us knowing that we are queens, that we are goddesses, and that we should be treated that way. And that people need to give us that place in their life if they want to be in our life."
The MTV Video Music Awards air live from New York City's Radio City Music Hall on Monday, Aug. 20 at 9 p.m. ET/PT.