ISO Hip, HQ Restaurant in Cambridge/Somerville/Arlington
I agree - live music AND good food are hard to come by under one roof. If you wanted to go across the river, I'd say Matt Murphy's probably combines all the factors you're looking for the best with a small but solid beer and drink selection, amazing food, and great live music (no cover charge). On the Cambridge side, the Middle East and TT's are where it's at for music (with PA's in Somerville coming close behind), but their food isn't anything to write home about. However, Central has an amazing array of "hip" spots to eat nearby. I.e. Miracle of Science is a good choice for local food and beer in a "hip" setting, and its right across the street from TT's/Middle East. Enormous room is a good choice for a group - you can get their Medi platter and a tasty drink. River Gods has great beer, a great (and veggie friendly) menu, and the sweetest bartender you'll ever meet. Green Street Grill is hip and legendary for their drinks, less so for their food, and no live music (that I know of). I suppose you could do Ryles in Inman for jazz, drinks and Southern food - but I've found that to be underwhelming, especially with 2 Chris Schlesinger restaurants nearby. So I think you have to decide what part of this equation is most important to you!
Adding live music to the mix makes it a pretty shallow pool, but a few ideas:
* River Gods (outside of Central Square) - solid upscale pub food, eclectic live music
* Central Kitchen/enormous room (Central Square) - enormous room is their upstairs lounge, primarily a DJ-centric place, they serve Middle Eastern-style shareable plates; Central Kitchen downstairs has no music, but is more of a dining destination
* Toad/Christopher's (Porter Square) - Christopher's does upscale pub food (I quite like their homemade veggie burger), they also own Toad next door, a pub featuring no-cover-charge live music nightly of the folk, blues, and bluegrass varieties
Three craft cocktail craft places to check out that don't feature live music, but do have tasty chow: Green Street (Central), Highland Kitchen (Somerville, near-ish to Union), and I agree with BoDubya on B-Side (near Kendall)
the plough and stars has all that and much more. although i wouldn't call it high end - i don't where you'll find high and live music though. and the plough clientel isn't just hipster turds - you'll find rockers mixing it up w/ MIT professors and sh1t. down the street you might want to take a look at the enormous room - younger and hipsterier. very cool vibe - lot's of lounging on pillows while gnoshing on small plates. good dj soundtrack in the background. and then there's b-side - they got the cocktail magic, the food has gone down hill a little bit though. but the place is kinda upscale....and free hard boiled eggs! that's friggin hip.