"Bo Diddley was one of the great rock innovators and was there at the beginning with Elvis, Chuck Berry, Little Richard and Buddy Holly. He was most known for inventing "The Bo Diddley Beat" a rhythm many have described as "shave-and-a-haircut, two-bits." He used that rhythm in hits like Hey! Bo Diddley and Who Do You Love, a song later covered by George Thorogood and the Destroyers. Buddy Holly used the beat in Not Fade Away and the Rolling Stones recorded Holly's song on one of their first albums.
The title of the album "Have Guitar - Will Travel (wire Bo Diddley)" is a take-off on a popular TV show of the time called Have Gun Will Travel about a pay-for-hire gunslinger named Paladin played by Richard Boone. Paladin's business card read "Have Gun, Will Travel - wire Paladin - San Francisco." Palladin had a horse; Bo is mounted on a funky pink-and-cream Vespa. (*update: see addendum: The scooter is most likely a 1957 Cushman Eagle.)
The Cushman company operated from 1903 to 2003. Most famous for golf carts, “Meter Maid” trucks, industrial and landscaping equipment etc., Cushman also made scooters from 1936 to 1965. They received a huge boost during WWII producing scooters for the war effort. These scooters were used on military bases, airfields, and were even “air-dropped” with the troops in the case of the Cushman “AIrborne”. Their most successful scooter was the Cushman “Eagle” which looked like a small conventional motorcycle."