Jennifer Lopez has gone a long way as a singer, actor, dancer, and entrepreneur. Since her breakthrough in the late 1990s, she’s been a force to be reckoned with. The actress now has her own beauty line, JLo Beauty, and has established herself as a global superstar.

All I Have: Celebrities used fur caps a lot back then, so it’s no surprise that JLo’s All I Have video featured one as well. Her cosmetics, like her headpiece, became iconic: smoky eyes and frosty lips.

Ain’t It Funny: Jenny wore a style inspired by a Spanish gypsy girl to show off her Latina ancestry. The bohemian style in the video was typified by wrap skirts, billowy tops, layered tribal necklaces, an arm cuff, and teased hair.

Play: if this song was played today in a club, we’d rush to the dance floor and groove to the beats. The song’s video, however, is what makes it stand out.

Love Don’t Cost A Thing: wears gold chain necklaces, aviators, high ponytails, and spaghetti shirts with low-rise slacks, channeling the ultimate throwback style. The charming song is about love and a lover’s discontent with his or her worldly desires. When it was released, the song became her first single to reach the top of the pop radio charts.

Jenny From The Block: On a road trip with our lady gang, this is one of the songs we’ve all blasted. Jenny From The Block, starring her current and then-boyfriend Ben Affleck, emanates the star’s confidence and demonstrates that no matter how famous she became, she would always keep to her roots.