Since it seemed timely, I chose to focus on candidates for the 2020 presidential race (including some past candidates). I decided to include songs that were "walk on songs" for candidates at their campaign launches, because these seem carefully chosen to project something about the candidates and their campaigns.
The original challenge list suggests this website as a source for information about campaign songs. The site includes not only official campaign songs, but all the songs associated with candidates: songs played at rallies, in commercials, and even in videos criticizing or parodying candidates. I searched for "walk on songs" and limited my search to campaign launch rallies.
To find more digital music scholarship, browse Harvard's list or check out one of the examples below.
You Shook Me All Campaign Long: Music in the 2016 Presidential Election and Beyond by 
Songs, Odes, Glees and Ballads: a bibliography of American presidential campaign songsters by 
Don't Stop Thinking about the Music: the politics of songs and musicians in Presidential campaigns by