Ratray started acting at the age of nine in the movie Where Are the Children? (1986). He starred as a child actor in various other programs and movies until his acting pinnacle in 1990 as Buzz McCallister, the mean older brother of Macaulay Culkin's character Kevin in Home Alone and Home Alone 2: Lost in New York, a role he later reprised in Home Sweet Home Alone (2021).
Ratray landed minor roles in Little Monsters (as Ronnie Coleman, the bully), Dennis the Menace (as Mickey, the boyfriend of one of Dennis's babysitters) and an episode as Martin in The Enforcers (1996). Another film role was The Prince and Me as the computer-obsessed roommate of Eddy, the royal Prince of Denmark. He was a regular improv actor on MTV's Damage Control, notably as a director of an erotic film called Crazy Motor Hos, in which he was dressed as a naval captain. Ratray appeared in the September 29, 2006 episode of Law & Order, "Avatar", as the mentally ill murderer Richard Elam. He later portrayed an antagonist in an episode of Law & Order: Special Victims Unit. He was a lisping doctor in the movie Slippery Slope (2006). He performed as Jimmy Link in Serial (2007). Ratray appeared in the 2009 film Surrogates as Bobby Saunders. Variety said "Ratray gets good mileage out of his role as a computer whiz too proud of his corpulent geekiness to consider a more glamorous substitute." In 2009, he was also a guest star on the fifth season of Supernatural in the episode "The Real Ghost Busters".
In late 2007, a documentary film crew followed Ratray's attempts to win the heart of US Secretary of State Condoleezza Rice. He used 'love disks' -- love letters set to music and images—to serenade her, and traveled from New York, to Alabama, Denver, Palo Alto and Washington, DC to court her. The resulting film, Courting Condi, was due for international release in fall 2008.

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