Jacob Ben Israel (Josh Sussman) from Glee vs. Neil Goldman from Family Guy

Via: Both are nerds in their high school attracted to a main character (Meg on Family guy and Rachel on Glee), have Jew-fros, wear thick rimmed glasses, have squeaky voices, use blackmail to try to get into their respective love-interests pants (unsuccessfully), and at one point report for a news agency. 

(Submitted by victorng)