CLIFFORD ELLIOTT is the "Golden Boy" of Capeside High Class of '99. The son of Robert Elliott, Capeside's physician, Cliff is varsity quarterback, student council chairman, top honor roll student, and regular Sunday attendee of First Church of the Nazarene. He often throws parties at his parents' beach house. He lives happily in this world, semi-oblivious to the pecking order. Cliff is actually a nice enough guy, who doesn't consciously assert his high school status, but not really aware of how others might experience high school. He also feels boring compared to Dawson Leery when dating Jen, who finds Cliff nice, but maybe not that interesting.
During his senior year, Cliff writes, produces, and directs a student film "Helmets of Glory" for Mr. Gold's film class. The autobiographical film chronicles Capeside High's previous football season, and is submitted to the Boston Film Festival (putting it in direct competition with Dawson's film). Cliff becomes enamored with sophomore Jennifer Lindley when she transfers to Capeside High from New York, and succeeds in scoring a date with her to the Victory Dance. After Jen breaks up with Dawson, Cliff heightens his pursuit of her, and she goes out with him (with her grandmother's approval) twice. Dawson's presence on both of those dates, and Jen's ambivalent feelings, prevent Cliff from actually developing a romance with her--the one damper on his otherwise perfect senior year.