Wood more than held his own against the once burgeoning boy icon Macauley Culkin in the clever and chilling "The Good Son" (1993). Playing a troubled son who recently lost his mother to illness, Wood gave an impressively nuanced performance encompassing loss, anger, and growing anxiety about the sadistic machinations of his twisted yet outwardly angelic cousin. He shifted gears to outlandish comedy as the star of Rob Reiner's "North" (1994) playing an apparently perfect child who, feeling underappreciated by his distracted parents (Jason Alexander and Julia Louis-Dreyfuss), becomes a free agent. Young North encountered an all-star supporting cast as he wandered the globe in search of more appropriate parents in this critically lambasted and commercially orphaned feature. The same year, Wood co-starred as Kevin Costner's son in the coming-of-age tale "The War". After a two year absence, he returned to the big screen in "Flipper" (1996), as a troubled youth, sent to live with his bohemian uncle, who encounters a boisterous dolphin. Wood followed with a fine portrayal of a troubled teen coming of age in the 70s in Ang Lee's superior "The Ice Storm" (1997).

Now of an age to play older teen roles, but possessing far more talent and experience than most of his contemporaries, Wood shied away from the high school-set romantic comedies and self-referential horror flicks that were inundating theaters in the late 1990s. When he did appear on the big screen in more exploitative projects, he managed to choose the best of the genres, taking featured roles in Mimi Leder's above-average Armageddon actioner "Deep Impact" and the Robert Rodriguez-directed, Kevin Williamson-scripted sharp and scary sci-fi thriller "The Faculty" (both 1998). A large part in the James Toback misfire "Black and White" (2000) didn't derail Wood, who instead emerged better for the effort, seeming more adult and more versatile after his work in the mostly-improvised, gritty drama. In 2001, he was featured in the Encore-aired independent "Life Without Dick" and followed with Edward Burns' "Ash Wednesday" (lensed 2001), playing the younger brother of the director-actor in this look at the Irish vs. Italian gang wars of the 1980s.

Cast in the long-awaited three-part feature adaptation of J.R.R. Tolkien's "The Lord of the Rings", Wood started a new chapter in his career. Having landed the sought-after part of Frodo Baggins, the actor was now a main player in a trilogy that was swarming with pre-release buzz. With "The Fellowship of the Ring" (2001), "The Two Towers" (2002) and "The Return of the King" (2003), Wood would become Frodo for three consecutive years in three blockbuster films. Thanks to his established versatility and remarkable talent, the actor was likely to meet a future career free from typecasting despite this primary role in the legendary fantasy franchise, while reaping the rewards of a starring role in a high-profile film.

Hot on the heels of the trilogy, Wood quickly appeared in his first non-Frodo role in the off-kilter but highly effective "Eternal Sunshine of the Spotless Mind" (2004), playing an ethically challenged lab technician who helps erase heartbreaking memories but then uses his knowledge of an unknowing former patient's (Kate Winslett) past relationship to woo her. He then had a chillingly silent turn as the cannibalistic, bespectacled serial killer Kevin Roarke in director Robert Rodriguez and writer-artist Frank Miller's visually arresting adaptation of Miller's crime noir comic book series "Sin City" (2005), appearing opposite Mickey Rourke in the segment "The Hard Goodbye."

Wood rounded out 2005 with “Everything is Illuminated,” playing a young man on a funny and rather bizarre journey to the Ukraine in search of what happened to the woman who saved his grandfather’s life when the Nazis destroyed the city where he was born during World War II. For the animated “Happy Feet” (2006), Wood provided the voice for Mumble, a vocally-challenged penguin who discovers his only chance at wooing a mate is through his slick dance moves. Then in “Bobby” (2006), first time director Emilio Estevez’s engaging look at the 16 hours prior to Senator Robert F. Kennedy’s assassination at the Ambassador Hotel in Los Angeles as seen through the eyes of several guests and employees. Wood played a young man about to be sent to fight in Vietnam who plans to marry a young woman (Lindsay Lohan) he barely knows.