In 1993, their first single "Baby Be Mine" was released on the soundtrack to the Universal Pictures comedy CB4 (starring Chris Rock). The song was written by Riley and Stonestreet and produced by Riley.Their debut album, Blackstreet, featured the singles "Booti Call", "Before I Let You Go" and "Joy". "Booti Call" and "Before I Let You Go" were both Top 40 hits, with "Before I Let You Go" hitting the Top 10. In 1996, they released their second album Another Level. It was a breakthrough success due to the top single "No Diggity" (with Dr. Dre), which was a No. 1 hit on the Billboard Hot 100 in November 1996. In 1998, Blackstreet won the Grammy Award for Best R&B Performance by a Duo or Group with Vocals.
Another Level eventually went four times platinum in the United States and peaked at No. 3 on the Billboard chart. "No Diggity" was later ranked at No. 91 on Rolling Stone and MTV: 100 Greatest Pop Songs. Another Level featured Mark Middleton and Eric Williams in place of Dave Hollister and Levi Little. Both Middleton and Williams were in groups prior to joining Blackstreet. Middleton was part of the short-lived Motown Records group Brik Citi. Williams was part of the trio The Flex, a group that sang on songs produced by their mentor Marley Marl. The success of Another Level landed them a guest appearance on Jay-Z's "The City Is Mine" and they teamed with Mýa and Mase for the hit "Take Me There" from the Rugrats soundtrack. The success of Another Level would also land them a spot on New Edition's 1997 Home Again reunion tour.
Blackstreet had a top ten album with Finally. The first single from the album, "Girlfriend/Boyfriend", was a collaboration with Janet Jackson featuring Ja Rule and Eve. Riley recorded a reunion album with Guy in 2000 and subsequently began working on material for his first solo record. Riley had second thoughts about disbanding Blackstreet and patched things up with Hannibal. Middleton and Williams returned to restore the Another Level lineup, and Riley's solo project became a Blackstreet reunion. After rumors of legal action and a preemptive countersuit, the group re-banded and released Level II.