Van Crosby was born into a blended family in Indianapolis, Indiana. He is the youngest of four siblings, which include Jordan Crosby, Zach Fite and Haley Fite. He relocated from Fishers, Indiana, to Los Angeles at the age of 2 and soon began working in the entertainment industry, following in the footsteps of his sister Haley.

Crosby appeared in his first national print job for Marsico Funds at 3 years old and his first national commercial at the age of 4 for Little Tikes. He has gone on to appear in several others over the years, including a recently aired Audi commercial. He has also guest starred in the series About a Boy and Criminal Minds.