On somebody’s tail Definition 1 of 2Pro Tip 1/3Physical Pursuit Used when describing someone physically close behind, like in a chase. I sprinted down the street with my brother on my tail. Pro Tip 2/3Not Literal It doesn't always mean a literal pursuit; it can describe a metaphorical chase. After the interview, I had several companies on my tail. Pro Tip 3/3Action Scenes Commonly used in action movies or books to describe thrilling chases. The hero raced through the crowd with the villain on his tail.