In the 1982 documentary, Return Engagement, Timothy Leary sits before a class of high school students and says, "I think that everyone in this room, in our lifetimes, can go through as many changes and metamorphosis and mutations, as the butterflies go from cocoons to caterpillars to beautiful high-flying creatures."
Leary's professional life was defined by a number of "metamorphosis and mutations." He was a clinical psychologist at the Kaiser Foundation in the 1950s, a spokesperson for the counter-culture movement in the 1960s, and an author reporting from prison in the 1970s. By 1980, Leary was 60 years old; almost eligible for social security, but not quite ready to leave the limelight. He embarked on yet another new career as a media personality and evangelist for technology. On the college lecture circuit, Leary encouraged students to explore mind expansion in cyberspace. His message of "Tune in, turn on and drop out" evolved into "Turn on, boot up, and jack in." 
After a speech at the University of Texas at Austin in 1981, Leary ran into a fellow lecturer and acquaintance from his past: G. Gordon Liddy. Leary and Liddy first encountered one another some 16 years earlier on opposites sides of a drug raid. In 1966, Leary was living at the Millbrook estate, a 64-room mansion in upstate New York. Peggy Hitchcock, an heir to the Mellon fortune and owner of the estate, invited Leary to use the property as a laboratory for psychedelic experimentation and communal living.
Millbrook residence, New York, undated
Hitchcock's neighbors, residents of the traditionally conservative Dutchess County, were miffed by Leary's presence and voiced their concerns to the local government. Liddy, an employee of the County's prosecutor's office, channeled the community's anger into action: he organized a nighttime raid on the Millbrook estate. Leary, recalling scenes from the raid in Return Engagement, said he awoke one evening to find a throng of policemen and Liddy (sporting a trench coat and signature mustache) outside his bedroom door. "Is that Peter Sellars as Inspector Clouseau?" Leary asked.
As fate would have it, Leary and Liddy would meet again under extraordinary circumstances. In the mid-1970s, both men were inmates at Terminal Island Federal Correctional Institution in California. Leary was incarcerated for marijuana possession and a prior escape from prison; Liddy for conspiracy, burglary and wiretapping in the Watergate affair.
By 1981, both Leary and Liddy had re-entered the public sphere as commentators on morning radio programs and talk shows. After their accidental reunion in Austin, Leary and Liddy decided to team-up as ideologues from opposite sides of the political spectrum; they embarked on a national tour of politically-themed debates, which would serve as the the basis for Return Engagement.
Throughout the film, Leary and Liddy tackle broad issues, such as national security and civil liberties, with provocative one-liners. "From time to time, for very good reason, this country engages in homicide," proclaims Liddy. "Every state is a mafia… I love America — it's the greatest mafia of them all," cries Leary.
While their rhetoric is acerbic, the relationship between Leary and Liddy is obviously good-natured. They laugh at each other's insults and banter about the events at Millbrook, like old friends reminiscing of youth.
Note written by Timothy Leary, undated
 Spertus, Ellen. "Escape Velocity: Cyberculture at the End of the Century." Technology Review 100, no. 3 (April 1997): 65-66.
 Arar, Yardena. "American Style: The Liddy and Leary Talking Circus." Associated Press. (Los Angeles, CA), August 5, 1982.
 Return Engagement. Directed by Alan Rudolph. Island Pictures, 1982.
 Rudolph, Return Engagement.