Roy Leonard

Tom Smothers, one half of the comedy duo The Smothers Brothers, has died at age 86. On March 27, 1974, Tom and Dick Smothers joined Roy Leonard in the WGN Radio studios for a conversation, including how they survived after being kicked off TV by CBS for being too political.

For decades, Dick Clark was the celebrity many people watched ring in the new year live from Times Square in New York City. Even today, nearly a decade after his passing, ABC’s New Year’s broadcast still uses Dick Clark’s name in its title. But, “America’s Oldest Teenager” was known for many other things beyond the […]

On January 8, 1986, at the height of the Bears Super Bowl run, the then-CBS NFL lead broadcast team of Pat Summerall and John Madden were in Chicago and made time to stop by the WGN Radio studios to visit with Roy Leonard. John Madden died today at age 85.

Fifty years ago, Clint Eastwood was already an established Hollywood star, having appeared in a number of movies and TV series. But in 1971, he would begin a new phase of his legendary career when he made his directorial debut with “Play Misty for Me.” On October 18, 1971, Clint Eastwood visited with WGN Radio’s […]

Ginger Rogers, one of the iconic stars of Hollywood’s “Golden Age,” was born 110 years ago this week, on July 16, 1911. The career of the actress, dancer and singer spanned decades. In the fall of 1991, Rogers visited the WGN Radio studios to visit with Roy Leonard and discuss her book, Ginger: My Story. Here […]

This week from the WGN Radio archives, we go back 35 years to June 4, 1986, a Wednesday morning on The Roy Leonard Show when he was visited in-studio by Donny and Marie Osmond. They were already veteran pop music superstars having had a variety show when they were teenagers and have continued over they […]

In this Roy Leonard segment from the early 1970s, Carol Channing is surprised to learn that Roy saw her in 1948, before she was a star. Channing died today at age 97.

Roy Clark, the country music legend and star of the long-running TV series “Hee Haw,” died today at age 85. In 1994, he visited with WGN Radio’s Roy Leonard to discuss the publication of his autobiography, My Life in Spite of Myself, and share memories from his long career. Here are a couple of minutes […]

Actor Burt Reynolds appeared a number of times on WGN Radio over the years, from the peak of his 1970s stardom to more recent appearances as he reflected on his career. Reynolds died today at age 82. We look back at some of his appearances here: Roy Leonard – March 1972, near the time of […]

America is remembering former First Lady Barbara Bush, the wife of the 41st President George H. W. Bush and mother of the 43rd President George W. Bush. Mrs. Bush died April 17, 2018 at age 92. On April 12, 1984, then Second Lady Barbara Bush stopped by the WGN Radio studios to visit with Roy […]

In this 1982 interview, Roy Leonard talks with comedy legend Jerry Lewis. Roy called it, “An amazing, serious interview about the art of comedy with one of the funniest men alive.” Lewis died August 20, 2017, at the age of 91.

Roy Leonard visits with Hollywood legend Debbie Reynolds, November 4, 1988. Reynolds died December 28, 2016, at the age of 84.

On the day after Thanksgiving, 1977, boxing legend Muhammad Ali visited the WGN Radio studios for an extended interview with Roy Leonard. Ali died Friday, June 3, 2016, at age 74. Click to download Recorded November 25, 1977

Friday, September 4th marks the one year anniversary of Roy Leonard’s passing.  In this podcast, Nick Digilio shares memories about his mentor and plays back some of the classic interviews Roy conducted (Sid Caesar, John Chancellor and Bob Hope.)  Plus a hilarious story involving Jerry Lewis! To hear the interviews in their entirety and other […]

Friday marks the one year anniversary of Roy Leonard’s passing. As part of a two day tribute, Nick Digilio welcomes Roy’s son Kelly to discuss his father’s legacy.

Dean talks shares memories of Roy Leonard with one of Roy’s favorite musical artists, Harry Conick Jr. [audio http://tribwgnfm.files.wordpress.com/2014/09/harry.mp3]

Dean chat’s with SNL’s Tim Kazurinksy, about his interactions with Roy Leonard. [audio http://tribwgnfm.files.wordpress.com/2014/09/kazurinsky.mp3]    

Dean talks with Actor, Brian Dennehy, about his memories of Roy Leonard. [audio http://tribwgnfm.files.wordpress.com/2014/09/dennehy.mp3]    

Dean talks about Roy behind the scenes with someone who knows best: his former producer, Andy Perez. [audio http://tribwgnfm.files.wordpress.com/2014/09/andyperez.mp3]    

Nick Digilio is joined by a roster of WGN colleagues past and present, including former Program Director Mary June Rose, Steve Bertrand, Steve King and Johnnie Putman, Spike O’ Dell,  Steve Cochran, VP of Creative and Programming Todd Manley, Lou Manfredini, Dean Richards, and John Williams to celebrate the life and work of the legendary […]

John Williams remembers WGN Radio Walk of Fame inductee, former host, and friend of the station, Roy Leonard along with WGN Radio Vice President of Content and Programming, Todd Manley, and fellow WGN Radio hosts Kathy O’Malley, Nick Digilio, and Lou Manfredini, as well as WGN Radio listeners and John McDonough, President and CEO of […]

Roy Leonard, a legendary interviewer and entertainment critic and a member of WGN Radio’s Walk of Fame, died Thursday night, his son Kelly confirmed to the Chicago Tribune.  He was 83. Leonard hosted middays on WGN Radio for over 30 years and interviewed celebrities and newsmakers. His soothing voice and calm demeanor made him a […]

More than forty years ago, Burt Reynolds made his first live appearances on the stage and on the Roy Leonard Show in Chicago. Here are some very entertaining memories. (March 15 & 29, 1972) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

WGN Radio Walk of Famer Roy Leonard joins Nick to talk about Sting’s musical, “The Last Ship”, and more.  George Karzas of the Gale Street Inn, Steve O’ Brien of Leadbelly Burgers and Michael Thornton of the Gift Theatre Company join the show to talk about a joint-venture, special edition burger available at both restaurants […]

The Tony Award-winning singer and actress in theatre, film and TV visited Roy several times, including this conversation from September 8, 1989. She was also an ambassador to the U.N. and prolific writer. Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

Newly minted WGN Radio Walk of Famer Roy Leonard makes his bi-weekly visit to the show to talk about the latest films and plays on his radar.  For more from Roy, check out his blog.  

The legendary Roy Leonard makes his bi-weekly visit to the Nick Digilio Show!  He gives his thoughts on “The Railway Man”, “Under the Skin”, “Heaven is for Real”, and more.  For more from Roy, visit his blog. [audio http://tribwgnfm.files.wordpress.com/2014/04/0419_roy.mp3]

The legendary Roy Leonard is back for his bi-weekly visit to the Nick Digilio Show.  He and Nick discuss the Cadillac Palace Theater’s production of “Peter and the Starcatcher”, George F. Will’s new book about the Cubs, and more. [audio http://tribwgnfm.files.wordpress.com/2014/04/0405_roy.mp3]

Jacques Cousteau was the most famous undersea explorer of the 20th Century. He visited Roy in 1978. Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

The legendary Roy Leonard calls in and tells us about “Shoot Me” with Elaine Stritch, “All the Way” with Bryan Cranston as Lyndon Johnson, and more.

Roy Leonard joins the show to share his thoughts on “The Lego Movie”, and the recent happenings in Chicago theatre.  Then we take a look at the regular features, “Drunks in the News’, “Straight Outta Context”, and “Nick D Spies”.

Roy visits with Ella Fitzgerald (1917-1996), the most popular jazz singer in the world for more than half a century. (February, 1977) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

We kick off a full Saturday night by catching up with Roy Leonard.  Public relations guru Richard Laermer checks in to give his take on Phillip Seymour Hoffman’s death, the upcoming Oscars, and more.

One of America’s great comedy writers, Larry Gelbart (TV’s M*A*S*H, the movie Tootsie and Broadway’s A Funny Thing Happened on the Way to the Forum) talks about growing up in Chicago and a great career helping to make other people funny. Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, […]

Nick kicks off a full Saturday night show with Roy Leonard, who shares his favorite films of the year.  Then, we hit Drunks in the News, Straight Outta Context and Nick D Spies.  

Animal rights advocate, social rights historian, novelist and television critic, Cleveland Amory dropped by on October 10, 1975, and even if you’ve never heard of him, you’ll laugh at his wit and be amazed at his knowledge. Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on […]

Northshore native Bill Murray talks about his early years at Second City and Saturday Night Live in this 1981 conversation with Roy. (June 19, 1981) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

Most Americans know her as Archie Bunker’s wife on TV’s “All In the Family.” But in this 1982 interview she tells Roy about her early career on Broadway and in movies and her one woman show where she portrays Eleanor Roosevelt. (May 6, 1982) Click here to return to the Roy Leonard Audio Archive. For more […]

In this 1978 interview, the man who makes so many people laugh shows a serious side and talks to Roy about his own family and how he’s bringing up his kids. He also talks to listeners and seems happy to answer their questions. (March 14, 1978) Click here to return to the Roy Leonard Audio Archive. […]

From about 1953 until 1980, Ray Rayner was one Chicago’s most popular television personalities starting at WBBM-TV as the host of a morning show called Rayner Shine. Rayner moved to WGN-TV in 1961 as Sergeant Pettibone, the host of The Dick Tracy Show, then on Bozo’s Circus as the clown Oliver O. Oliver and then his […]

Did he really say “Nice guys finish last”? In this 1975 interview, Leo answers the question and offers some insights into the game of baseball and a lot about the Cubs. Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

From singing with Benny Goodman to her hits “Fever” and “Is That All There Is?,” Peggy Lee tells it all. (April 19, 1988) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

In one of many appearances on the Roy Leonard Show, Dick talks about the origins of “American Bandstand” and why Elvis never appeared on the show. (November 8, 1985) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit Roy on ChicagoNow.com.

The great NBA star came by in 1991 to talk about his book, “A View from Above,” and proved to be a fascinating guest. Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit royleonard.com.

Harry Connick, Jr. tells how he got hired to record the “When Harry Met Sally” songs, talks about the influence of growing up in New Orleans, and reveals how he quit smoking. (1990)

The great movie star Ginger Rogers talks about dancing with Fred Astaire and her many Hollywood relationships. (1991) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit royleonard.com.

James Taylor introduces his new album and talks about how he gets his ideas and writes his songs. (November 19, 1985) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit royleonard.com.

Sid Caesar talks about his drug problems and shares great stories about Mel Brooks, Larry Gelbart and Carl Reiner. (November 16, 1983) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit royleonard.com.

Debbie Reynolds tells how she lost $21 million and took ten years to pay it off, plus highlights from her singing and acting career. (November 4, 1988) Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit royleonard.com.

Jackie Mason, a man whose made a career out of insulting people. Do people ever get mad at him? Listen to this 1992 interview Click here to return to the Roy Leonard Audio Archive. For more about Roy Leonard, visit royleonard.com.