You got this young guy who tries to scam goods and services out of businesses for free. The show had him pretending to have a TV makeover show - “Extreme Homeless Makeover”. He was able to get free limo services, a complete makeover at a high-end salon, and free clothes.
All in all, a weak show. Typical of Comedy Central (who either have great shows - MST3K & South Park, or lousy shows - Tough Crowd).