Possessive of Quoted Song Title in Quotes
Solution 1:
Song titles can be italicised, and that would make this far less awkward.
Hey Jude’s popularity reached unprecedented heights in 1968.
Better still to reword it to avoid the possessive altogether, though.
Solution 2:
It looks funny, but I believe that's correct. Putting the possessive inside the quotes is the only alternative, and that would be wrong.