dinner on sunset
I assume you're looking for something closer to Fairfax/Crescent Heights and the comedy clubs.
Pinches is decent, and I've also heard good things about Mexico on Santa Monica, but El Compadre might be another option if you're looking for sit-down casual but close.
The new Baby Blues on Santa Monica off Fairfax is great too. Depends what your definition of trendy is though. The place is very popular, but pretty chill.
El Compadre Restaurant
7408 W Sunset Blvd, Los Angeles, CA 90046
Baby Blues BBQ
7953 Santa Monica Blvd, West Hollywood, CA 90046
Also....an old reliable....Greenblatt's. It's good, solid deli fare, but what makes it interesting is the wine list. Jeff's got a terrific selection of wines by the glass....or you can buy a bottle from the adjoining store. (great selection. some prices are high, but he's got very good sales)
And there's parking in the back.
For a chili dog or salad try Carney;s