I should give Malick another shot. I love film, but only first tried him when I was much younger (Thin Red Line) and don’t think I really got it.
Never tried Tree of Life or any of his more recent stuff.
Got any recommendations in the first 2-3 of his you’d suggest?
I recommend turning on subtitles for Tree of Life. There's a lot of random whispered voice-overs, and without subs you'll have no idea who is speaking, let alone what they are saying.
Or dive at the deep end and watch Knight of Cups or A Hidden Life. You will either like it or not, frankly I don't think it matters what you'll see first, I love all of his movies even though I didn't understand Thin Red Line when I was 20. But Knight of Cups hit me hard when I was 36.
Badlands and Days of Heaven are definitely his most conventional films and thus good starting points. Badlands especially is a great film, Days of Heaven is a bit uneven in terms of plot and pacing, but the cinematography is beautiful.
Then you have The Thin Red Line and The New World, which to me feel like a transitional period between the more conventional films and The Tree of Life, which is the first film that is characterized through and through by Malick's extremely divisive style. I personally love The Thin Red Line, but I can see why it's not for everyone. (I would skip The New World.) All later films have a very recognizable style, for which I think The Tree of Life is the best starting point.
Long story short: I'd start with Badlands, then watch The Thin Red Line, then The Tree of Life. If you like the last one, watch any of his later films.