By September of 1988, Davitt Sigerson of Rolling Stone was calling Al B. Sure! the best of the "hip-hop love men," describing him as a modern crossover artist who blends rap's pulsing beat with jazzy romantic crooning. "Nite and Day" won over even the toughest critics, like J. D. Considine of Musician, who allowed that the single had "insinuating appeal," but disparagingly called Sure! a "hip-hop Barry White."

In early 1989, Sure!'s career hit the kind of snag that could have ruined him: he was charged with rape in Los Angeles. Although he was cleared of the charges by April, Nelson George, writing in Billboard, wondered whether Sure! could recover his carefully wrought image: "Although the media worked during the last year to turn the 20-year-old vocalist into a sex symbol, it's not surprising that it loved the idea of connecting him to a sex scandal. That the story proved groundless, unfortunately, isn't as sexy."
By June of 1989, Sure!'s "If I'm Not Your Lover" had critics gushing with praise. Within 16 months, the single "Misunderstanding" (co-produced by Eddie F. of Heavy D and the Boyz), from Sure!'s second album, Private Times ... and the Whole Nine, was a Number One R&B hit. As the singer told Janine McAdams in Billboard, "I think when people hear the album they'll see that this is very much my growth process from album one [In Effect Mode] to album two.... It's nothing like album one and has nothing to do with album one."

Sure!'s second album clearly reflects his growing confidence as an artist, as in his duet with Diana Ross on "No Matter What You Do," a song he had written when he was a junior in high school. And his covers of the Eagles' "Hotel California," which begin and end the album, intrigued many listeners, including Amy Linden of Rolling Stone. In her review of Private Times, she called the "Hotel California" remake a "creepy combination of Lifestyles of the Rich and Famous and Dark Shadows," that demonstrates "an element of risk absent from the rest of the LP."

By this time, however, Sure! was seriously developing his longstanding interest in producing music. He had already co-written and co-produced three tracks with DeVante Swing of the group Jodeci and by 1993 had done similar work with artists like Tevin Campbell, Chaka Khan, Robert Palmer, Michael McDonald, Rod Stewart, and Al Green.

Sure! was also planning to start his own label, Suretime Records. In late 1992, Sure! released his third album, Sexy Versus, another mixture of slow romantic cuts and high-speed hip-hop, featuring Grand Puba, Slick Rick, Rakim, and Chubb Rock (who had also appeared on Private Times). Sure! described the album to Jennifer Perry of the Source as "adult contemporary hip-hop" and told EM magazine that it "cover[s] every aspect of what love is, from promiscuity to shyness to anger to infatuation to teasing games. The whole thing." He even underscores the importance of safe sex in his romantic ballad "You and I," explaining to EM: "No matter how hot the moment of passion is, you still have to take care of your business."

Again, Sure!'s brand of bedroom hip-hop met with mixed critical response, though in January of 1993 he was voted best male R&B vocalist at the New York Music Awards. This honor confirmed Al B. Sure!, who planned to release a new album late in 1994, as a consummate "modern musician," equally skilled at his own craft and at bringing the best out of other artists. His fresh, sexy sound has popularized a new kind of hip-hop--one that is mellower, with as much emphasis on melody as beat. As Sure! told McAdams: "It was something that I've always kind of felt naturally. If you have [a] melody and you're really saying something in the song, you can't lose."

In 2010, Sure! appeared as one of the 12 contestants on the TV One reality television dating game show The Ultimate Merger. The series was produced by Donald Trump and starred former Apprentice contestant Omarosa Manigault-Stallworth, whom Sure! dated previously.