25 Bizarre Musical Collaborations

Tony Bennett is a legendary singer of traditional pop standards, jazz, and show tunes. He is known for collaborating with many modern artists and continues to be active at the age of 95, and despite a diagnosis of Alzheimer’s disease. John Mayer has produced countless albums and is well known for his vocals as well as ability on the guitar. The two sing this Johnny Mercer-Harold Arlen standard, made famous by Frank Sinatra, on Bennett’s “Duets II” album. The album features several other great performances with artists like Amy Winehouse, Willie Nelson, and Mariah Carey.

Trace Adkins is a country musician who’s been active for almost 40 years. Keb’ Mo’ is known for his own original style of postmodern blues. And Stevie Wonder is, well, Stevie Wonder — one of the great and most versatile musical talents of our age. “Memory to Memphis” is sung by Adkins with Keb’ Mo on guitar and Wonder on harmonica.

Yankovic is known for his parodies of popular songs and for creating wacky new ones of his own. Winslet is known for her acting career, encompassing everything from “Titanic” to “Mare of Eastown.” She and Yankovic sing this song from the CD accompanying Sandra Boynton’s book “Dog Train: A Wild Ride on the rock-and-Roll Side.” While musically it may not be the most astounding work, “I Need a Nap” focuses on a message that we can all get on board with.

Willie Nelson, one of the originators of “outlaw country” and both an actor and an activist, is famous for long hair, weed, and a disdain for authority. Wynton Marsalis is a jazz legend who has won just about every accolade a musician can, including the first Pulitzer Prize in Music given to a jazz musician. The two teamed up to create an entire album that combines both of their unique styles on a range of blues, country, and pop songs. Marsalis even sings a bit.

Two icons came together to make music for the entire family when cello legend Yo Yo Ma — who has appeared on “Sesame Street” numerous times to help inspire the younger generations to take up music — tried to teach Elmo how to play the fiddle while showing off a little of his own talents.