In 1984 he became an agent at ICM Artists the classical music division of International Creative Management (representing artist including YoYo Ma, Isaac Stern and Itzhak Perlman as well as the worlds top tour Symphony Orchestras and recital artists.). In early 1985 he reestablished ICM Lecture division representing internationally acclaimed Politicians, authors, and personalities for the arts and entertainment industry (President Jimmy Carter, Arthur Miller, E.L. Doctor, Douglas Fairbanks Jr. and Dominick Dunne.) In 1986 he was hired by the William Morris Agency where he was Senior Agent in charge the lecture division. He worked with the department heads of the Literary, Television, Motion Picture, Theater and Music Departments to representing President Gerald Ford, Dr. C Everett Koop, Tom Clancy, Tom Browkaw, Rudolph Giuliani and Lauren Bacall. He was also instrumental in the representation of Apollo 13 astronaut James Lovell ‘s book, movie deal (Lost Moon the Apollo 13 Story) and his lecture tours. While at William Morris Mr. Chaplin established the Symphonic Pops department coordinating the Symphony tours for such artists as Aretha Franklin, Ray Charles, The Temptations, The Four Tops, among others.

After leaving the William Morris Agency he opened his own company Chaplin Entertainment Inc. in 1994. Chaplin Entertainment Inc. is considered one of the premier boutique agencies specializing in booking contemporary music artists to perform individually tailored programs with symphony orchestras throughout North America. Over the past several years, Chaplin Entertainment has booked tours for Liza Minnelli Al Jarreau, Michael Bolton, Olivia Newton John, Amy Grant, Dionne Warwick, Ben E. King, Frank Sinatra Jr., Three Dog Night, Kansas, James Darren, and Jose Feliciano.

Chaplin Entertainment also Manages Kadiatou Diallo, the Mother of Amadou Diallo the 23 year old African student who was gunned down by New York City Police officers by 41 bullets in February of 1999. Mrs. Diallo wrote a book telling her son Amadou’s story "MY Heart Will Cross This Ocean." She is also a big draw on the college lecture circuit preaching peace and social and racial tolerance in society. Randy is also managing a exciting new recording artist Kelly King. Kelly has toured with Al Green, Dolly Parton, Vince Gill, Amy Grant and Brenda Lee. She has also starred several Broadway and Off Broadway shows.