In the entertainment world, jazz was the choice of music, and a couple popular musicians include Paul Whiteman and Duke Ellington. The first portable radio was introduced in 1923 and Time Magazine was launched. Silent movies and Broadway shows were also very popular.
As for transportation, the Model T by Ford made up over half of the vehicles on the road by the mid-1920's. Chrysler was introduced by Maxwell Motor Company. Chevrolet, Cadillac and BMW start producing vehicles at this time as well.
However, there were some down parts when it came to the Roaring Twenties. Prohibition (the ban of alcohol) lasted the entire decade and caused "Speakeasies" (similar to a underground saloon kept on the DL) to pop up. Crimes associated with the mob were numerous as well. The sugar industry plummeted in the early 20's, causing Hershey's to go bankrupt. The Roaring Twenties came to a screaming holt when the stock market crashed in 1929.
sources: thepeoplehistory.com; answers.com