Benson was assigned to travel with The Beatles on their inaugural American tour in 1964. One of his most recognisable images shows the band in a gleeful pillow fight at the hotel Georges V in Paris. Other celebrities Benson has photographed include Bobby Fischer, Michael Jackson, who allowed him access to his bedroom, and Elizabeth Taylor, whom Benson photographed before and after her brain surgery. He has also photographed political figures, including every U.S. president since Dwight D. Eisenhower, and covered war zones. Benson was standing next to Robert F. Kennedy when the senator was shot on 5 June 1968 and has remarked on the difficulty of steeling himself to document the historic moment: "I kept telling myself 'this is for history, pull yourself together, fail tomorrow, not today.'"