So I'll try and make my answer a bit more entertaining since I feel my top 5 for both scenarios are the same and the items are kinda boring. So Ill just assume that I have a knife, gun, fire starting, water purifying, and cover. Ill choose some stuff that I have in my urban and woods gear that might be different than some peoples.
Urban: Silcock key, Lock picks, portable power-bank, EOD bar, Add-a-lock.
This stuff is always in my EDC bag. I have a pretty extensive get home system in my truck. This is my "I gotta walk and things arent wonderful" stuff. Practice if you want to lock pick. Im pretty decent, but I dont want to take the time to single pin pick, so all of my picks in this kit are rakes, rockers, and lock bypass tools. EOD bar is from CountyComm, just a nice flat little pry bar. And add a lock is for if I break a lock and dont want anyone in behind me. All this assumes that I need to find shelter somewhere for the night in an office or warehouse and smashing a window isnt a good idea.
Woods: Tyvek ground cloth, Kevlar cord, DJI Spark Drone, Tenkara Fly Rod, Garmin Dog GPS
All this is pretty self explanatory. The spark is a cool little drone. Decent range and picture and very portable. Tenkara is a very packable fly fishing system. And the Garmin GPS is great to both track my dog (hunting) and for navigation for myself.