Long wasn't out of work for long. First time director F. Gary Gray offered her a strong comedic role as Debbie, the foxy neighbor who becomes the object of Ice T's affection, in the sassy comedy "Friday" (1995). Another novice, Theodore Wicher, gave the actress her first real lead in “Love Jones" (1997), as a photographer who has an on-again, off-again relationship with a writer (Larenz Tate). Long and Tate generated real screen heat and both earned high marks from critics. The actress followed with the sleeper hit "Soul Food" (also 1997), playing the youngest of a trio of sisters, a newlywed struggling with her career as a hair stylist and the demands of her marriage to an ex-con (Mekhi Phifer) trying to go straight. After appearing in a pair of urban-oriented action-thrillers, "Butter" (1998) and "In Too Deep" (1999), Long appeared in the predominantly African American ensemble of writer-director Malcolm Lee's "The Best Man" as the one-that-got-away old flame who reunites with her otherwise committed ex (Taye Diggs) at the wedding of a mutual friend, played the club hopping best friend of Patricia Arquette in the horror-thriller "Stigmata," starred opposite Jamie Foxx in the hostage comedy "Held Up" and appeared opposite Colin Firth in the low-profile indie "The Secret Laughter of Women" (all 1999). Long next appeared as Mary McCormack's lesbian girlfriend in the gay-themed ensemble drama "The Broken Hearts Club: A Romantic Comedy"; as a empathetic receptionist who shares a bond with Giovanni Ribisi in "Boiler Room"; played a member of a protective circle of lesbians in the HBO telepic "If These Walls Could Talk 2"; and played Martin Lawrence's love interest/faux granddaughter in the comedy "Big Momma's House" (all 2000).

After the middling haunted house film "Sightings: Heartland Ghost" (2002) and joining the cast of the NBC drama "Third Watch" in 2003, she scored as Melvin Van Peebles lover Sandra in "Baadasssss!" (2004) writer-director Mario van Peebles' well-received account of the making of his father's breakthrough film. She was also enticing in her supporting role in the 2004 remake of "Alfie," playing the should-be-forbidden girlfriend of Alfie's (Jude Law) best friend (Omar Epps) who proves too great a temptation. In the family-friendly “Are We There Yet?” (2005), she had a small, thankless role as a devoted mother of two children taken on a road trip by a smooth operator (Ice Cube) intent on getting a date with her. Long’s considerable talents were wasted in a role giving her little to do. And despite being panned by critics, “Are We There Yet?” opened number one at the box office and subsequently filled the coffers at Sony Pictures.