IMHO, you need two things for “deep talk”: authenticity and vulnerability. You can’t have that level of connection without both individuals bringing those to the table. I, personally, don’t get to that level flippantly–only with people I know and trust can reciprocate. If you try to force it, you get the opposite: shallowness.

Jonathan Coultan is my favorite singer-songwriter, ever. He’s drifted away from “comedy” songs recently, but he’s still fantastic. He’s able to perfectly straddle funny and sad, somehow.

He’s had a few brushes with more widespread notoriety, too: he wrote “Still Alive” and “Want You Gone” for Portal 1 & 2, the opening song to the show “Brain Dead,” the theme song to RiffTrax, and a great cover of “Baby Got Back” that Glee ripped off without crediting him.

Highly recommend!!!