Forgettable video store fare like "Address Unknown", "The Paper Brigade" and "Robo Warriors" (all 1996) were among Howard's early credits, but guest roles on "Chicago Hope" (CBS, 1996) and "Home Improvement" (ABC, 1997) proved more substantial. In 1998, after playing Ron Silver's son in the HBO-aired thriller "Skeletons" (1997), Howard took a role where he would call Robert Urich dad, playing the son of the ship's captain on the UPN remake series "Love Boat: The Next Wave". While a largely unimpressive series, "Love Boat: The Next Wave" offered Howard weekly exposure, and helped him to win many new fans. When the ship docked permanently in 1999, the young actor hit the big screen in the talking tot misfire "Baby Geniuses", but recovered the following year as one of three boys enrolled in an otherwise all-girls high school in the Fox summer sitcom "The Opposite Sex". While the series was certainly more engaging than much of its competition, it quickly left the airwaves.
That fall, Howard recovered with a regular role on "Grosse Point", a series spoofing the behind-the-scenes and on screen antics of a teen soap opera reminiscent of creator Darren Star's former baby, "Beverly Hills, 90210" (Fox). Here he played Dave May, the stand-in and partner in crime of doltish teen heartthrob Johnny Bishop (Al Santos). A bit racier than his previous offerings, "Grosse Pointe" would introduce Howard to an older, edgier audience. Also in 2000, the actor was featured in the CBS TV-movie "Yesterday's Children", playing a contemporary young man whose mother (Jane Seymour) becomes obsessed by lifelike dreams of a struggling woman in 1930s Ireland.