Reminisce about old school R&B singers and groups who had — and some still have — a reputation for being bad boys.

1. Case

Case was known to be a hustler trying to make ends meet to become a singer. The edgy R&B singer had near-fatal shooting accident that put a short halt on his career, but he bounced back. “Touch Me, Tease Me” and “Missing You” are a couple of his hits from the ’90s.

2. Pretty Ricky

Even though Pretty Ricky started out in the late ’90s, the group’s success came later with hip-hop hits such as “Grind With Me,” “On the Hotline,” and “Your Body.” This bad boy group initially included Corey ‘Slick’em’ Mathis, Ala Diamond ‘Baby Blue’ Smith, ‘Spectacular’ Blue Smith, and Marcus ‘Pleasure P’ Cooper.

3. Montell Jordan

Guilt by association! Montell Jordan was the primary male solo artist on Def Jam’s edgy Def Soul label, but we remember him well for his chart-topping hit, “This Is How We Do It.”

4. H-Town

This group, founded in 1990 by twin brothers Keven ‘Dino’ Conner and Solomon ‘Shazam’ Conner, and their longtime friend Darry ‘GI’ Jackson. No one from this decade will ever forget their R&B #1 single, “Knockin’ Da Boots.”

5. Keith Sweat

Photo by Peter Pakvis/Redferns

Another innovator of the New Jack Swing sound, Keith Sweat was never shy to about turning it out on stage while performing his hits. Who could forget “I Want Her,” “Make It Last Forever” and “Make You Sweat.” We see you, Keith.

6. BBD (Bell Biv DeVoe)

We knew them as part of New Edition, but when they broke out on their own, Bell Biv DeVoe hit it big with “Poison.” And every since then, we “never trust a big butt and a smile.”

7. Sisqo

We really don’t have to say much about Sisqo except… “Thong, thong, thong, thong, thong!” He may recall that he started out as a member of Dru Hill.

8. Guy

One of the major go-to New Jack Swing producers, Teddy Riley started Guy in 1987 with Aaron Hall, and Damon Hall replacing Riley’s childhood friend, Timmy Gatling, before the group’s self-titled debut album was released in June 1988. “Groove Me” and “Spend the Night” were a couple hits. Riley produced other bad boy R&B groups such as Blackstreet and Wreckx-n-Effect. Remember “Rump Shaker?”

9. Jodeci

Sean ‘P. Diddy’ Combs help groomed Jodeci’s bad boy image under the Uptown record label. From drunken moments caught on surveillance cameras to rumors of domestic abuse, DeVante Swing, Mr. Dalvin and K-Ci and JoJo held true to that image at times, but still managed to create great hits such as “Forever My Lady” and “Come and Talk to Me.”

10. Bobby Brown

From “Every Little Step” to “Tenderoni,” Bobby Brown is a certified bad boy of R&B. Remember when he received citations for engaging in lewd conduct for pretending to engage in sexual activity with female audience members onstage? For that reason and for his previous run-ins with the po-po, we had to include him on this unofficial list.