Conversation so far:
What was Macaulay Culkin's breakthrough?
Culkin rose to fame with his lead role of Kevin McCallister in the highly successful blockbuster Christmas film, Home Alone.
Did he win any awards for the role?
He was nominated for a Golden Globe Award, and won an American Comedy Award and a Young Artist Award for his role as Kevin McCallister.
Did he have any other movies during this time?
In 1991, Culkin starred in an animated Saturday morning cartoon television series, Wish Kid, hosted Saturday Night Live and starred in Michael Jackson's "Black or White" music video.
Did he work with any other celebrities?
My Girl (1991), for which he was nominated for Best On-Screen Duo and won Best Kiss at the MTV Movie Awards, with Anna Chlumsky.
Is there anything else interesting?
He reprised his role of Kevin McCallister in the sequel, Home Alone 2: Lost in New York (1992.
Was that movie successful?
he was nominated for a Kids' Choice Award.

Question: What was his biggest role?
Self-contained rewrite: What was Culkin's biggest role?