Dennis Dugan: Richie Brockelman, Captain Freedom and more

Dennis Dugan in a guest spot as private investigator Richie Brockelman in "The Rockford Files".

Source: https://www.imdb.com/title/tt0071042/characters/nm0240797/

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What would you do if a crook strong-armed your dad and essentially stole his business with no recourse. Especially if you are a good-natured, college-educated, happy-go-lucky kind of guy?

Private Investigator Richie Brockelman decides he is going to get even, and get some money for his dad, by running a con on the crook.

The challenge is, Richie really doesn’t know what he’s doing. Looking on is his old friend Jim Rockford, a seasoned private investigator who knows his way around a con. He ultimately helps Richie get even, and get some money back for Mr. Brockelman.

This is my favourite episode all time of “The Rockford Files”, because it is so well written and because Richie Brockelman is a compelling character.

Dennis Dugan played Richie Brockelman, and went on to a couple other memorable performances for me, before settling into a career as a director, most often of Adam Sandler movies.

It was Dugan’s birthday a few days ago, offering a great chance to look at Richie Brockelman, Captain Freedom, and Ronald Miller's dad in “Can’t Buy me Love”.

Richie Brockelman, Private Eye
Dennis Dugan got his start on television, with guest spots in shows such as “The Waltons”; “Cannon”; “M*A*S*H”; and “Columbo”.

In 1978, he played Richie Brockelman in a two-part episode of “The Rockford Files” called “The House on Willis Avenue”, which served as a pilot for a TV show. In it, Rockford meets Brockelman, a 22-year-old private investigator he teams up with to investigate the death of a fellow private investigator.

I recall seeing that, then hearing about the new series called, fittingly, “Richie Brockelman, Private Eye”. It was on Channel 7 of the peasant vision dial at like 9 p.m. or 10 p.m., the last show anyway, before the news. It was hard to find, but I do recall seeing a couple episodes.

My outstanding memory of the show was that Richie was a recently graduated college student, who drove a convertible and, when trying to figure something out, would say, “The thing of it is…”

Sadly, “Richie Brockelman, Private Eye”, lasted just five episodes and was not picked up for another season.

However, the next year, Richie Brockelman was back one last time in the “Rockford Files” episode “Never Send a Boy King to Do a Man’s Job” in 1979. It is one of my favourite episodes of any series ever. Richie’s dad is bilked out of his business by Harold Jack Coombs, a ruthless businessman. Everything is legal, so Richie wants to run a con to get at least some of his dad’s money back. Ultimately, Rockford gets involved, becomes a major part of the con masquerading as high roller Jimmy-Joe Meeker, and successfully cons Coombs.

It was my favourite memory of Dennis Dugan, but would not be the last.

Space age
The next time I saw Dennis Dugan, he was playing an astronaut who is hurtled back in time to King Arthur’s Court, where he helps defend the king from a plot to de-throne him. It was a Disney movie that came out in 1979 called “Unidentified Flying Oddball.” It was also called “A Spaceman in King Arthur’s Court.”

He would appear in the 1981 Joe Dante horror film “The Howling”, and an episode of “Supertrain”, before another defining role as an actor.

Super hero – sort of
Criminals flee a crime scene in a vehicle when suddenly a man in super hero costume jumps in front of the car holding out his hand to stop. The criminals veer to avoid him crash, and are apprehended.

Captain Freedom has nabbed his first criminals.

Dennis Dugan played Captain Freedom in four episodes of the groundbreaking police drama “Hill Street Blues” in 1982. Captain Freedom was delusional, but the police, especially undercover cop Mick Belker, took a liking to him. Sadly, he is eventually killed trying to foil a crime, and dies in Belker’s arms.

Empire and Shadow Chasers
Dugan also had recurring roles in two TV series that did not last long.

“Empire” came out in 1984 on Channel 13 of the peasant vision dial, and was a satire of corporate life. Dugan played the straight man in a world of intrigue. “Empire” lasted just six episodes before being cancelled.

A friend of mine referred to “Shadow Chasers” as a live action version of Scooby-Doo. The show came out in November of 1985, and lasted just 14 episodes, although only 10 aired. Dugan played a reporter teamed with a British anthropologist, played by Trevor Eve, who investigate paranormal activity.

I saw “Empire”, but “Shadow Chasers” never aired on peasant vision. I only heard about the show, and its demise, on “Entertainment Tonight”.

Daddy dearest
Dennis Dugan went from being the college kid to the wise dad in the wink of an eye.

“Can’t Buy Me Love”, my favourite movie, came out in 1987. It is the story of Ronald Miller who, tired of being on the outside looking in, pays the most popular girl in school $1,000 to go out with him. He gambles it will be his ticket to the in-crowd, and he is right – initially.

Dennis Dugan plays Ronald’s dad David Miller. He offers Ronald his not-too-cool station wagon, complete with his business name “Tic Tac Tile” stencilled on the side, any time he wants to take it out. At first Ronald cringes, but later is seen in it – with “Tic Tac Tile” conveniently covered up.

It was a great supporting role.

Rest of the decade
Dennis Dugan rounded out the ‘80s with roles in the movies “She’s Having a Baby”; “The New Adventures of Pippi Longstocking”; and “Parenthood.”

He also had steady TV work with guest spots in “Hunter”; “Wiseguy”; and five episodes of “Moonlighting” as star Cybill Shepherd’s short-lived husband.

The years after
Dugan kept acting, with movies such as “Problem Child”; “Happy Gilmore”; “Big Daddy”; “The Benchwarmers”; “Grown Ups”; “That’s My Boy”; “Grown Ups 2”; and more. “Happy Gilmore 2” is scheduled to come out in 2025.

He was on television in “Doogie Howser, M.D.”; “Columbo”; “L.A. Law”; “NYPD Blue”; “Burke’s Law”; “Picket Fences”; “Chicago Hope”; “Love Boat: The Next Wave”; “Ally McBeal”; “Hope and Faith”; and much more.

Dugan also moved into directing, with projects such as “Problem Child”; “Brain Donors”; “Happy Gilmore”; “Beverly Hills Ninja”; “Big Daddy”; “Saving Silverman”; “National Security”; “The Benchwarmers”; “I Now Pronounce You Chuck and Larry”; “You Don’t Mess With the Zohan”; “Grown Ups”; “Just Go With It”; “Jack and Jill”; “Grown Ups 2”; and “Love, Weddings and Other Disasters”.

Parting thoughts
It is hard to believe Dennis Dugan is 78 years old, because he will always be frozen in time as 22-year-old Private Investigator Richie Brockelman. He had this “Aw shucks” charm that caused people to underestimate him and allow him to solve tough cases.

That same boyish charm made Captain Freedom so endearing on “Hill Street Blues”. It even melted the heart of the toughest cop on the beat, who genuinely grieved when Captain Freedom died.

Even when he graduated to playing the father of the main character in “Can’t Buy Me Love”, he still had an affable charm.

Put it all together and Dennis Dugan had a pretty good career in the ‘80s.