Hey I'm probably Springsteen fan #3 on this site behind other Chris (cshadows) and Craig, so I'll speak to this.
In my opinion at least (and many others'), Born to Run
is always going to be the best album recommend to 98% of people as an entry point to the Springsteen catalog (the other 2% being those rare breeds who only dig Nebraska
of his work). The reason for that is simple: it's his best album. It also contains some of his most instantly recognizable (and best) songs, and is the most concise and clear encapsulation of what Bruce is and what his music represents. Sure that has changed somewhat from album to album over time, but there's a reason people's minds always jump to Born to Run
when they think of Bruce: it's the most critical piece of the Springsteen story.
That being said, I absolutely understand where you're coming from in rec'ing Wrecking Ball
to him, in terms of the sound of the album alone. It is a great record and has some moments that sound a lot like what he's looking for. I'm gonna have to take issue with you suggesting it's arguably his best vocal work though. Not knocking his vocals on the record obviously.....but goddamn man you can't stack it up against Darkness
and expect it to come out on top haha.
Speaking of, I would recommend Darkness on the Edge of Town
and The River
(particularly the first half) as other places for him to look in the Springsteen catalog based upon what we know he likes.
Anyway, that's that.