How do you light these types of shots?

for the sky, use a polarizer filter and point your camera at the sky 90 degrees to the sun. An additional graded ND can be useful if the floor is too dark, which seems unlikely in this setting. For the shadows use one or two silver reflectors.
 
For a feature film of that budget, there are many possibilities. You can use a massive overhead silk to diffuse the sunlight and then use large HMIs shooting through diffusions to shape the subject. It's also possible that it was just an overcast day, so they only focused on lighting the actor and the sky was later added in post. On a low budget the options are quite limited. Polarizers help, but they really only take a stop off the sky which is barely anything. Reflectors is very "sourcy," and hard to control, plus if your talent is in the shade the bounced light will be way too warm. A graduated ND filter can be helpful but doesn't work for every angle.
 
Light your subject to be about 1/2 to 1 stop brighter than the sky, then expose for your subject,
this will saturate the sky by underexposer to the sky AKA your backgroung.
 
http://youtu.be/vcn2GOuZCKI @ 0:35 and http://www.youtube.com/watch?v=3Lr_RSkIlE4 at 0:35-:43, 1:27, 1:35, my main concerns are how they got diminished shadows on so many peoples faces close to an edge of a building and it the second how they postitioned a light to have the colors in the sky to be so vibrant while the talent is lit.

There's a couple of ways... pay Helios to be in the right place at the right time... if he is indisposed... screening/bounce, filters, and if one has the budget, big lights to compete with Helios, and post production, 'cleaning' up colors to look more brilliant...

As for what a pro production did... all of the above...

What you can do on a less than budget... select a god spot, some screening and bounce of the sun, filters, and some post production clean up or enhancements.
 
The Fast Five is shot on an overcast day. You can see the sky a little in the left and the shadows are very soft. The Bow Wow video is definitely green screen.
 
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