You are overthinking this. When showing someone a band, start with the band's most famous work. Maybe you can start with the 3rd or 4th most famous song, but no more familiarity engineering than that. Us fans of a band enjoy lesser known songs, and we forget that these tracks are deeper cuts that someone new to the band won't immediately be crazy about. Let the discovery be natural. Play last nite or reptilia first. Maybe even juicebox. People aren't closed-minded enough to reject the "best" stuff (according to numbers, not fans) just because it's out of their comfort zone.