>>79924251Tom Petty first appeared as Lucky as just one bit-part redneck in the Kahn episode you mentioned, and seemed to have the fewest lines compared to the other two.
Season 8/9 marked the time Brittney Murphy returned as a regular cast member (after season 4 she focused more on movies and had to phone in all her lines, meaning Luanne appeared rarely for a few seasons), and I guess they wanted something new to do with her character and so decided on her eventually marrying. I have no idea how it really went down, but I guess they figured it'd be cool to use a side character from an earlier episode and have a celebrity guest voice, so they chose Lucky for the part.
It might be that he and Mike Judge were already bros; I know Tom Petty is friendly with a few of the VAs, but I don't know if that was the case before he began working with them. Either way, he said he was a fan of the show before appearing in it, and described Luanne as "hot" in some random interview.
No idea about the song.
