(written from a Production point of view)
Benjamin's acting debut was a guest shot on Beauty & the Beast in the 1988 episode "A Happy Life" starring Ron Perlman and Armin Shimerman, the same year as his appearance on TNG. That year also contained Benjamin's film debut in the Billy Crystal led comedy film Memories of Me with Larry Cedar and Cory Danziger. In 1989 he appeared in All's Fair with Sally Kellerman and alongside Nick Dimitri, Joseph Ruskin, Marshall Teague and Nicholas Worth in the television film Original Sin. In 1990 he worked on the television movie Call Me Anna reuniting with Cory Danziger as well as Timothy Carhart and Richard Fancy. Benjamin's third film role was in the 1993 biopic Barbarians at the Gate in which he portrayed future millionaire H. Ross Johnson in the scenes depicting Johnson's childhood. Also appearing in this film are Raye Birk, Ron Canada, Joanna Cassidy, Bruce French, Mark Harelik and Jeanne Mori.
Benjamin only worked on the big screen twice in the 1990s. His first cinematic work was in Ice Cream Man (1995) with Clint Howard and David Warner. The other being his final acting work altogether, 1996's Storybook with Ed Begley, Jr., Robert Costanzo, James Doohan and Heather Lauren Olson. Benjamin's remaining television work consisted by guest roles on Cheers starring Kirstie Alley, Kelsey Grammer and Bebe Neuwirth in the 1991 episode "Pitch It Again, Sam", with Henry Woronicz and on Empty Nest in the 1992 episode "It's Not Easy Being Green" with Shannon Cochran and Harvey Vernon. He had recurring roles such as portraying the young Kevin Arnold on The Wonder Years starring Olivia d'Abo in 1988 and 1989 and the other being Bobby Porter on the short-lived series Get a Life in 1990, with Michael G. Hagerty, Graham Jarvis and Tracey Walter in his first episode and John Walter Davis in his second one.