He also played a role in She's All That as Laney's younger brother, Simon.
He continued acting as a child and teenager, mainly working in comedies, including Home Alone 2: Lost in New York and Father of the Bride and its sequel.
In 2015, he portrayed Rye Gerhardt in the second season of the critically acclaimed FX series Fargo. He has four brothers: Shane (born 1976), Macaulay (born 1980), Christian (born 1987), and Rory (born 1989), and sister Quinn (born 1984).
His sister Dakota (born 1979), died in a car accident in 2008.
Macaulay married actress Rachel Miner when he was just 18, but the pair split two years later.
He has also endured personal tragedies, including the death of sister Dakota in a car crash, and half-sister Jennifer Adamson from a drug overdose.