Bob Lilly was born on August 17, 1933, in Dallas, Texas. He was commissioned a 2d Lt through the Air Force ROTC program at the University of Texas on January 30, 1956, and completed Undergraduate Pilot Training in May 1957. Lt Lilly next went through Helicopter Pilot Training at Randolph AFB, Texas, and graduated in October 1957. He flew with the 551st Operations Squadron at Otis AFB, Massachusetts, from October 1957 to April 1959. His next assignment was with the 22nd Helicopter Squadron and then the 4082nd Operations Squadron at Goose AB, Labrador, from April 1959 to March 1960. Lilly flew with the 28th Operations Squadron at Ellsworth AFB, South Dakota, from March 1960 to October 1961, and then with the Western Air Rescue Center at Glasgow AFB, Montana, from October 1961 to August 1964. He next flew CH-3's with the Environmental Awareness Research Center at Patrick AFB, Florida, from August 1964 to October 1965, when he went to Southeast Asia. Lilly began flying combat missions out of Udorn AB, Thailand, in October 1965, and he was shot down over North Vietnam and taken as a Prisoner of War on November 6, 1965. After spending 2,655 days in captivity, Colonel Lilly was released during Operation Homecoming on February 12, 1973. After repatriation, he served as a Liaison Officer at Wright-Patterson AFB, Ohio. His final assignment was at Squadron Officer School at Maxwell AFB, Alabama, where he retired from the Air Force on November 30, 1980. Bob Lilly died on October 12, 2007, and was buried at the Alabama Heritage Cemetery in Montgomery, Alabama.

His 1st (of 3) Silver Star Citation reads:

Captain Warren R. Lilly distinguished himself by gallantry in connection with military operations against an opposing armed force as Aircraft Commander over North Vietnam on 6 November 1965. On that date, Captain Lilly displayed an outstanding degree of courage and devotion to duty as he voluntarily flew an unarmed and extremely vulnerable rescue aircraft into a hostile area known to contain numerous concentrations of heavy antiaircraft weapons in a valiant attempt to rescue a downed USAF pilot. As he entered the recovery area, Captain Lilly's aircraft encountered heavy ground fire and burst into flames, causing him and his crew members to bail out over hostile territory. By his gallantry and devotion to duty, Captain Lilly has reflected great credit upon himself and the United States Air Force.