Same Love, it's about how gay people are often targeted and that it's not shameful- kind of a coming out to yourself song.
Otherside, it's about addiction and loss. This one wrecks me as someone who's grappled with addiction, and has lost two of my closest people to addiction.
Thrift Shopping may have been his big hit, but he's always been dedicated to rapping about things that are on the serious side.