Singer: Louis Armstrong

Nicknamed “Satchmo,” Louis Armstrong was a crossover artist before people knew such a thing existed. It’s probably a stretch to say that he brought jazz to the mainstream, but not much of one. He was certainly the most engaging and accessible ambassador of the emerging American musical genre.

Like many entertainers of his generation, he began by singing on street corners for pennies and nickles. Then he took up the trumpet, and the rest, as they say, is geography. His career arc took him from New Orleans to Chicago to Harlem. He was on a musical journey as well, finding his way from true jazz to jazz-influenced pop to popular hits.

He was the first great trumpet soloist in jazz, and he kept his signature handkerchief ready to mop his brow. Younger audiences today know him for his 1968 recording of “What a Wonderful World”, featured in such movies as Madagascar and Meet Joe Black. But his biggest hit was “Hello Dolly.” Released in 1964, it knocked the Beatles out of the top spot on the chart, and Armstrong remains the oldest person ever to have a number one hit.

By the way, apparently he got the nickname “Satchmo” because of his large mouth. Yeah, I don’t get it either.