I just love that place! We are so lucky here in LA to have something that cool.
Nice company, bottle of wine, Blanket, stars in the sky, and cool live music. Now that, is living!

The Greek Theatre is about half the size of the Hollywood Bowl and therefore more intimate.  You have more of a connection to the artist playing there.

Yes had a client there take me there once it was really cool, except for the traffic, I am generally a beach person, but never had a client want to take me to the beach, Any takers let me know lol

Hwood Bowl is phenomenal. I just saw Fantasia performed there, complete with crazy fireworks during the Nutcracker Suite. They even included an amazing collaboration between Dali and Disney! Definitely one of the coolest attractions (institutions?) LA has to offer.

Fireworks, of course

though there are Hollywood Bowl-type events at Disney Hall. Unfortunately, you'll have to wait until next year for the outdoor experience.

Saw Carlos Santana a few weeks ago...warm beautiful evening, not an empty seat in the place, so traffic was definitely something to deal with.  But if you can just chill with as you mentioned, great company, then the wine, the blanket, the stars in the sky, and enjoying the time..always worth it and pretty hard to top the Bowl.

Saw the Eagles twice at HB last year. It was awesome.