Picking up any of Bryson's dozens of books is like attending your college's most interesting lecture taught by the most delightful, witty professor. He's written on everything from the summer of 1927 to his experience walking the Appalachian Trail, but my favorite is this one, which is about Americana, and how we got all of the words associated with it, like Uncle Sam and Yankee Doodle. There's a whole chapter on Hollywood, including stories of how all of the '30s starlets picked their stage names, and others about shopping, advertising, and sports.
This, along with another Bryson book about language called The Mother Tongue, were my favorite car trip books, aka ones I would read aloud to my parents as we went on day trips to battlefields and historic towns (seriously, my brand is strong). The whole thing is written in such an engaging way that pretty much every sentence made me say, "Oh my god, I never knew that!" as I read it, which is truly the sign of a great book. Americana (and etymology) comes up a lot on Jeopardy!, more so than you might realize, and I'm so happy I basically memorized this book years ago.
Get it from Amazon for $3.61+, Barnes & Noble for $1.99+, or a local bookseller through IndieBound here.
Words are good, and you don't need to be a spelling bee champ to appreciate them! If you want to branch out from just the history of English, try The Language Instinct or Empires of the Word.