NOW: Chilli went on to pursue a solo career alongside her releases with TLC. She also starred on several reality shows, most recently appearing on Girls Cruise in 2019. More recently, she made headlines by going Instagram official with Matthew Lawrence.
3.THEN: After rising to fame as Ricky in Boyz n the Hood, Morris Chestnut went onto play notable roles in shows like C-16: FBI and movies like The Best Man.
NOW: In 2022, he reprised the role of Lance Sullivan in The Best Man: The Final Chapters. He also got a star on the Hollywood Walk of Fame.
4.THEN: Naomi Campbell was one of only six models to earn the title of "supermodel." However, she was heralded as "the reigning megamodel of them all."
NOW: In 2022, the University for the Creative Arts awarded her an honorary doctorate for the global impact she made on the fashion industry. Then, she rang in 2023 with her daughter, who was born in 2021.
5.THEN: Will Smith began his acting career starring on The Fresh Prince of Bel-Air and set a personal goal to become "the biggest movie star in the world." Alongside launching his solo music career, he starred in movies like Independence Day and Men in Black.
NOW: In 2022, he won a string of Best Actor awards for King Richard, including an Oscar, a BAFTA, and a Golden Globe. He also began executive producing the Fresh Prince reimagined drama Bel-Air. His film Emancipation premiered at the end of the year.
6.THEN: Karyn Parsons played Hilary Banks on The Fresh Prince of Bel-Air.
NOW: In 2005, she launched Sweet Blackberry, a content company that educates children about the unsung heroes of Black history. In 2019, she published her debut novel, How High the Moon. She also authored two picture books — Flying Free: How Bessie Coleman's Dreams Took Flight in 2020 and Saving the Day in 2021.
7.THEN: Halfway through the first season of Family Matters, Jaleel White guest starred as Steve Urkel. The character was so popular that he became a series regular.
NOW: In 2021, he launched a cannabis brand called ItsPurpl, which includes variants of the "Purple Urkle" strain. He also continued to act, appearing in movies like Hustle (2022) and shows like Family Reunion (2021).
8.THEN: Lark Voorhies played Lisa Turtle on Saved by the Bell. She also guest starred on Family Matters and The Fresh Prince of Bel-Air.
NOW: From 2020 to 2021, she reprised her role on Peacock's Saved by the Bell revival.
9.THEN: In the '90s, Brandy earned eight Grammy nominations. In 1999, she won the award for Best R&B Performance by a Duo or Group with Vocals for "The Boy Is Mine" with Monica. She also starred in the sitcom Moesha and the movie Cinderella.
10.THEN: In the early '90s, Queen Latifah earned four Grammy nominations for Best Rap Solo Performance, and she finally won in '95. Meanwhile, she starred on the sitcom Living Single then launched her talk show The Queen Latifah Show.
NOW: She's starred on and executive produced the crime drama The Equalizer since 2021.
11.THEN: After responding to an audition call in a magazine ad, Mel B (whose real name is Melanie Brown) joined the Spice Girls. Nicknamed Scary Spice, she was part of the best-selling girl group of all time.
NOW: In 2022, she was appointed a Member of the Order of the British Empire for service to survivors of domestic violence. Later that year, she got engaged to Rory McPhee.
12.THEN: Tia Mowry had a starring role on Sister, Sister alongside her twin sister Tamera.
NOW: From 2019-2022, she starred on the Netflix sitcom Family Reunion. In 2021, she published her second cookbook, Quick Fix Kitchen, and released a houseware line, Spice by Tia Mowry, with Gibson. In 2022, she announced her separation from her husband, Cory Hardrict, but celebrated their marriage as a success.
13.THEN: Alongside her twin sister Tia, Tamera Mowry starred on the sitcom Sister, Sister.
NOW: In 2020, Tamera Mowry-Housley signed an overall deal with Crown Media, the company that owns the Hallmark Channel. Since then, she's been in Hallmark movies and hosted the talk show Home & Family until its cancellation in 2021. She's also hosted the HGTV competition show Table Wars since 2021.
14.THEN: Already a massively successful artist, Janet Jackson embarked on her Rhythm Nation World Tour in 1990. It became the most successful debut tour in history. She then signed a new record deal with Virgin Records, which made her the highest-paid recording artist at the time. She continued to make history with multiple chart-topping albums and singles.
NOW: In early 2022, Janet released a two-part tell-all documentary, in which she discussed the negative impact the wardrobe malfunction that Justin Timberlake caused during their 2004 Super Bowl halftime performance had on her career. In 2023, she's embarking on the Together Again tour. She also promised that she has new music coming.
15.THEN: Toni Braxton started her music career with her sisters as a member of The Braxtons, but she released her self-titled debut solo album in 1993. It went #1 on the Billboard charts and won her three Grammys. Her second album, Secrets, won two more Grammys. She also made her Broadway debut playing Belle in Disney's Beauty and the Beast.
NOW: In 2020, Toni signed a new record deal with Island Records and released her 10th album, Spell My Name. In 2021, she competed on The Masked Singer, and in 2022, she starred in the Lifetime movie Fallen Angels Murder Club.
16.THEN: Haddaway's debut single, "What Is Love," reached #1 on the charts in 13 countries.
NOW: He released his latest single, "And Now," in 2021.
17.THEN: Lauryn Hill rose to musical prominence with the Fugees, whose sophomore album, The Score, topped the Billboard 200 and won two Grammys. After the band split, she released her legendary solo album, The Miseducation of Lauryn Hill, which won five Grammys. It's still celebrated for bringing hip-hop to the mainstream and opening new doors for women in music.
NOW: Lauryn famously never released another album, but she's occasionally released singles over the years. Most recently, she was featured on Teyana Taylor's 2020 track "We Got Love" and Nas's 2021 single "Nobody."
18.THEN: Missy Elliott started her music career as part of Sista but released her acclaimed debut solo album, Supa Dupa Fly, in 1997. She also became known for her frequent collaborations with Timbaland.
NOW: In 2021, she became the first female rapper inducted into the Songwriters Hall of Fame. She also received a star on the Hollywood Walk of Fame. In 2022, her hometown of Portsmouth, Virginia renamed a portion of McLean Street to Missy Elliott Boulevard in her honor.
19.THEN: Beyoncé rose to fame as a member of Destiny's Child. The group found immense success toward the end of the decade with singles like "Bills, Bills, Bills" and "No, No, No."
NOW: As a solo artist, Beyoncé became a cultural icon. Her most recent release was the highly anticipated 2022 album Renaissance. It was her seventh album in a row to debut at #1 on the Billboard charts.
20.THEN: Tyra Banks's modeling career started off strong when she booked 25 shows during her 1991 Paris Fashion Week debut. She was the first Black woman on the covers of both GQ and the Sports Illustrated Swimsuit Issue. She was also the first Black Victoria's Secret contract model and cover model.
NOW: Since 2020, Tyra's been hosting Dancing with the Stars.
21.THEN: And finally, Samuel L. Jackson played mainly minor roles until 1991's Jungle Fever. He went on to play key roles in some of the most iconic films of the decade, including Jurassic Park, Pulp Fiction (which earned him an Oscar nom), and Star Wars: Episode I — The Phantom Menace.
NOW: In 2022, he received an Honorary Academy Award, a lifetime achievement award that was presented by Denzel Washington. In 2023, he's set to reprise the role of Nick Fury in two Marvel productions — the miniseries Secret Invasion and the movie The Marvels.