In the mid- to late 80s, Sena began to emerge as a top director in music videos, then still an upcoming and uniquely inventive form. The director worked with such top-selling artists as Sting, Richard Marx and Bryan Adams, but is best remembered for directing a number of clips starring Janet Jackson. Working closely with Jackson, Sena helped to define the artist's career through her memorable videos and did his part to elevate the singer to pop icon. Their collaborative oeuvre serves as a timeline of Jackson's work, showcasing her personal as well as creative development from virginal American sweetheart ("Let's Wait Awhile", 1987) to playful adult ("Miss You Much", 1989); a meditative solo artist finding her footing ("The Pleasure Principle", 1987) to a revolutionary leading her dancing troops ("Rhythm Nation", 1989), and from broken hearted pleader ("Come Back to Me", 1989) to self-possessed seductress ("If", 1993). The dramatic flair and dark visuals utilized by Sena were appropriate for Jackson's image. The choreography-focused, controlled representations of their 80s work pointed towards Jackson's level-headed, studied perfection and served as a cue to her mysterious private persona. When she came out of her bag with 1993's "janet", Sena's work followed suit, and they together proclaimed her new freedom with the vibrant, sexually charged urgency of "If".
In 1993, Sena made his feature directorial debut with "Kalifornia", a vivid and violent depiction of a serial killer (Brad Pitt) on a road tour with his childlike girlfriend (Juliette Lewis) and a well-off photographer/writer couple (Michelle Forbes and David Duchovny). Evocative and chilling, the film had as many detractors as supporters, with audiences and critics alike split over whether the film was an important look at the brutality of human nature or a dangerously sensationalistic bloodbath. Despite, or perhaps because of the controversy stirred up by "Kalifornia", Sena disappeared from the big screen and returned to the more anonymous world of television commercial work. His exceptional visual approach and knack for capturing the popular imagination led to continued success in the field, winning top advertising awards and earning a place for many of his commercials in the permanent collection at the Museum of Modern Art.
2000 saw the director return to features with the remake of former employer Halicki's debut feature "Gone in 60 Seconds", a 1974 cult classic that boasted a 40-minute car chase sequence. Sena's update of this chronicle of a particularly crucial night in the life of a car theft ring featured hot properties Nicolas Cage, Angelina Jolie and Giovanni Ribisi in starring roles. Informed by his music video and commercial work, Sena posited a take on the film that was visually adventurous, with inspired and thematically significant use of brilliant color, and an inventive approach to shooting action sequences. Similar in grittiness to "Kalifornia" although not nearly as brutal, "Gone in 60 Seconds" was the helmer's chance at increased credibility. Undoubtedly he also hoped it would firmly establish him as a director capable of working in various media like his peers Michael Bay and David Fincher. As the film awaited its box office and critical fate, Sena had his eye on future developing projects, including the action thrillers "Worst Case Scenario", "Sleeping Dogs" and "Swordfish" (2001).