Padalecki had an uncredited role as a high school bully in 2003's comedy Cheaper by the Dozen, which he played after being asked by fellow actor and friend Tom Welling, who played Charlie Baker, and the director of the movie, who wanted someone larger than Charlie to pick on him.
Padalecki mendapatkan peran tanpa nama sebagai anak sekolah nakal di film komedi tahun 2003, Cheaper by the Dozen, di mana dia berperan setelah diminta oleh rekan aktor dan temannya Tom Welling, yang memerankan Charlie Baker, dan sutradara film itu, yang menginginkan seseorang yang lebih besar daripada Charlie untuk mengganggu Charlie.