The World’s Toughest Milkman

David Boswell and Reid Fleming are topics that I have wanted to write about for some time. The reason why I haven’t already profiled the “world’s toughest milkman” is that I had been unable to procure a specimen of the second of Boswell’s two early self-published works, Heartbreak Comics, until this past December. One of my contacts in Saint John, NB, sourced a couple of copies of the original printing for me. As soon as I had the comic in my hands on Christmas Eve, I knew that it was time to give Boswell and Fleming the Forgotten Silver treatment.

David E. Boswell was born in London, Ontario in 1953, but grew up in Hamilton and Dundas. He graduated from Sheridan College in 1974 and subsequently worked as a dark room technician before moving to Vancouver, BC, in 1977, where he still lives today. In Vancouver, Boswell got his big break as a professional cartoonist drawing “Heart Break Comics” strips for the seminal underground newspaper The Georgia Straight. Boswell’s work first appeared in issue # 504 (July 14, 1977) of the publication. His initial strip was well received and had thirty-four instalments. In 1978, he debuted Reid Fleming in The Georgia Straight in his own series. The character was a hit and the new series of strips ran almost weekly until early 1979 when issue # 600 was released and was dubbed the “last” issue of the series. In reality, the newspaper was rebranded as the Vancouver Free Press in order to shed negative connotations associated with The Georgia Straight name, as the “hippie” newspaper had been the subject of public and government scrutiny throughout the decade. The rebranding led to the newspaper becoming more of a mainstream publication with a progressive slant that was focused particularly on music news. The name change was not successful and, ultimately, the paper returned to its original moniker in March 1981 (and continues to be published today).

This Reid Fleming strip originally appeared in The Georgia Straight # 579 (December 28, 1978). It is reprinted on page # 18 of 1980’s Reid Fleming, World’s Toughest Milkman. Imaged sourced from David Boswell’s Twitter account.

The popularity of Reid Fleming led to Boswell self-publishing his first comic book in 1980, Reid Fleming, World’s Toughest Milkman. The comic features an introduction by Bob Mercer, the former editor of The Georgia Straight. From what I understand, most (if not all) of the strips in this comic are reprinted from the underground newspaper. The first printing of Reid Fleming # 1 had a print run of 10,000 copies, which was a gutsy move considering that Boswell did not have a distribution deal. However, Ron Turner from Last Gasp learned about the comic, ordered five hundred copies, and quickly sold out. Last Gasp kept ordering more and more. Eventually, the comic sold well enough that Boswell released a second print run. The first printing can be identified by the $2.00 cover price (as second prints were $2.50).

Cover of 1980’s Reid Fleming, World’s Toughest Milkman # 1. This is a first printing. Artwork by David Boswell. Image from my personal collection.

Reid Fleming, World’s Toughest Milkman follows the adventures of the surly, reckless and aggressive title character as he delivers milk to customers, gets into scraps and tells people off, while often hanging out with his co-worker Lowell Cooper (aka “Captain Coffee”) and interacting with his love interest, Lena. In the very first strip (which is perhaps the best known), Fleming threatens an elderly customer by suggesting that he will urinate on her flowers if she doesn’t pay the 78 cents she owes for the milk. All of this happens to the chagrin of his supervisor, Mr. Crabbe, who would prefer to fire Reid Fleming. However, the owner of the company, Mr. O’Clock, is just as happy to dock Fleming’s pay cheques for damaging property (like milk trucks) and other indiscretions.

This very meta strip called “Ken Worm & Jerry” appears on the back cover of Reid Fleming, World’s Toughest Milkman # 1. This is a great example of the type of humour that Boswell excels at. Image from my personal collection.

Despite the success of the comic, a new Reid Fleming title would not be released for another six years. Boswell’s next comic would be Heartbreak Comics, which is advertised on the inside back cover of Reid Fleming # 1. Apparently, things didn’t go according to plan, as the new comic would not appear until 1984. The new comic featured all-new artwork and did not reprint strips from The Georgia Straight. Reid Fleming appears in the comic as the primary antagonist.

Cover of 1984’s Heartbreak Comics. This is a first printing. Artwork by David Boswell. Image from my personal collection.

Heartbreak Comics follows the adventures of private detectives Laszlo (aka the “great” Hungarian lover) and Ken. The comic begins with Laszlo having an affair with Lena Fleming when the pair are nearly caught in the act by Reid Fleming. A suspicious Reid eventually finds moustache wax in his bathroom and hires Ken to investigate who is having an affair with his wife.

Laszlo has an address book filled with the names and numbers of the various women he is courting, but he decides he wants to be monogamous after Ken hires the woman of his dreams, Constance, to work as their secretary. He throws the address book away (which Ken quickly saves for his own purposes). Meanwhile, Reid Fleming gets into a scrap with the police and is sent to prison.

Later, Laszlo and Ken attend a masquerade, where a jealous Laszlo sees Constance dancing with a man dressed as Hitler. He assaults the man and is sent to jail himself where he encounters Reid Fleming, but is able to keep his prior affair with Lena secret.

During Laszlo’s time in jail, Ken starts stalking Constance (as a peeping Tom), while Constance starts dating a barber (who is depicted as an adult ventriloquist doll). All the while, Laszlo fantasizes about his future life with Constance, who he assumes he will continue seeing after he gets out of prison.

The comic culminates in Reid Fleming figuring out that Laszlo is the person who Lena was seeing, just as Laszlo learns that Constance is in a relationship with someone else. Reid and Laszlo fight each other while Constance watches. Ken intervenes but is knocked out by Fleming, who then sees Lena driving around the neighbourhood with a different mystery man and decides to follow her. Constance slams the door in Laszlo’s face, as Ken reveals that he still has the address book. The comic ends with Laszlo meeting with a different woman from his address book for a sexual rendezvous. The entire comic is filled with surreal humour and excellent artwork.

Back cover of Heartbreak Comics advertising a second issue of Reid Fleming, World’s Toughest Milkman. Ultimately, Boswell would not self-publish a second issue of the series. Instead, Eclipse would reprint the first issue and then release a five-issue second volume of new material beginning in 1986. Image from my personal collection.

A second issue of Reid Fleming, World’s Toughest Milkman is advertised on the back of Heartbreak Comics but was not self-published by Boswell. Instead, in 1986, Boswell came to an agreement with the American publisher Eclipse to release his comics. Eclipse would reprint the 1980 Reid Fleming comic three times. The Eclipse editions have the Eclipse logo at the top left of the cover and a cover price of $2.50 and are easily differentiated from Boswell’s self-published editions because of said logo.

Afterwards, Eclipse would publish a five-issue second volume of Reid Fleming, World’s Toughest Milkman from 1986-1990. This new story arc is called “Rogue to Riches.” The series was successful enough that the early issues had multiple print runs. This was followed by a 180-page graphic novel in 1991 called Fun with Reid Fleming (which reprinted much of the earlier work).

Cover of 1986’s Reid Fleming, World’s Toughest Milkman # 1 from Eclipse, which debuts the new miniseries “Rogue to Riches.” This is a first printing. Image from my personal collection.

Unfortunately, Eclipse went out of business shortly afterwards and the character was left in limbo for several years. This changed in 1996 when Boswell brought the characters back under the imprint Deep-Sea Comics. The new company reprinted the original 1980 issue of Reid Fleming, World’s Toughest Milkman and all of the Eclipse issues too (with the “Rogue to Riches” series now being renumbered as issues # 2-6). Deep-Sea also reprinted the 1984 Heartbreak Comics one-shot and released a softcover graphic novel called Origins of Reid Fleming, World’s Toughest Milkman, which reprinted all of the original strips from The Georgia Straight. Beyond this, Deep-Sea released three new issues of Reid Fleming (issues # 7-9) from 1997-1998 and a new one-shot called Ray-Mond was released towards the end of 1998. Unfortunately, the new run of Reid Fleming comics was intended to be a five-issue miniseries, but issues # 10 and 11 were not released at the time.

Cover of 2002’s Flaming Carrot Comics # 32. Artwork by David Boswell with a script by Bob Burden. Image from my personal collection.

Reid Fleming would disappear for several more years, before resurfacing at Dark Horse in 2002 as part of a team-up with Bob Burden’s Flaming Carrot. The comic actually serves as Flaming Carrot Comics # 32 (a series which had its own very interesting printing history). When I was an undergraduate in Fredericton twenty years ago, I was really into the Flaming Carrot and this comic was my introduction to Reid Fleming. I still have the copy that I bought off the shelves at Strange Adventures back then.

Fleming would disappear again for a number of years until IDW released a hardcover graphic novel reprinting many of the Reid Fleming stories in December 2010. In 2011, Boswell was inducted into the Doug Wright Awards’ Canadian Cartoonist Hall of Fame, which brought a brand new set of eyes to Reid Fleming. IDW was supposed to release a second collection of Reid Fleming comics, but this never came to fruition.

In 2015, director Charlie Tyrell released a short documentary about Boswell and Reid Fleming called I Thought I Told You to Shut Up! The film is narrated by Jonathan Demme and features interviews with Ed Asner, Matt Groening, Jeff Loeb, Dave Thomas, Kevin Pollak, Bob Mercer, Colin Upton, Calum Johnston, and Boswell himself. The short film explains how the character’s film rights were purchased by Warner Bros. in the 1980s. Since Boswell sold the film rights, rather than optioning them, he sold the character in perpetuity to Warner Brothers. Boswell wrote a script, but the film was never made and has been in development hell ever since. Actors such as Dave Thomas, Jack Nicholson, Bob Hoskins, Robin Williams, and Jim Belushi were linked to playing the character at different times. Ultimately, Boswell was screwed by Hollywood. Yet, as Groening says in the film, “David is one of those guys who’s underappreciated and underacknowledged.” I highly recommend giving the film a watch: everybody loves Reid Fleming.

The Trailer Park Boys and Reid Fleming crossover in this comic strip from 2017 that was written by Calum Johnston and drawn by David Boswell. Image sourced from Strange Adventures.

In the years since, Cal Johnston and Boswell released a strip featuring Reid Fleming and the Trailer Park Boys. Boswell has also continued to actively promote the character on his website, where various types of swag and memorabilia are available for sale. He is also active on both Twitter and Facebook. There is also a public fan group on Facebook that boasts more than 1,000 members. As such, Reid Fleming still has a good amount of fandom for a character that debuted more than forty years ago, but never gained a mainstream audience.

To the delight of many, Boswell began offering digital download and print versions of issue # 10 of Reid Fleming, World’s Toughest Milkman in December 2021. The new issue continues the unfinished story from the 1990s Deep-Sea Comics run. The print version of the comic has a hefty price tag of $49.99 USD plus shipping, but from what I understand this comic is hand-made and is made to order using high-end materials. Given the price, I expect that this comic will be quite rare down the road. I haven’t yet made the purchase, but I will likely do so sometime soon.

Reid Fleming continues to be one of the most popular and influential characters from the Canadian Silver Age. Unlike many of the comics, creators, and characters that I have profiled over the years, it is inaccurate to describe Reid Fleming as “forgotten.” Nevertheless, David Boswell and his characters continue to be overlooked by mainstream audiences within and outside of the world of comic books. If you have not taken the time to read any of Boswell’s comics, I highly recommend that you do so.

brian Campbell
brian Campbell

Dr. brian Campbell is an Anthropologist based in Halifax, Nova Scotia, Canada. His PhD research focused on the used-goods trade in Halifax. Dr. Campbell is co-owner of East Coast Toys and Games, one of Atlantic Canada's largest eBay stores specializing in pop culture collectibles. Dr. Campbell left academia in 2019 to focus on his business. During his spare time, he researches Canadian comics that were released between 1960-1990.

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mel taylor
mel taylor
1 year ago

Hey brian
I have always thought Upton and Boswell were the cream of the Vancouver crop (or a Fleet Street law firm). Ried Fleming was so damned good I don’t even have any copies left after “lending” them out to other fans! Sic transit gloria mundi, I guess. Now, I’m wondering where you’re going to start with Colin Upton since he has created so many hundreds of different minis over the years, all of them worthy of consideration, and all of them still in print! I sent him $30 for a sampling of his minis a while back, and was blown away when I recieved a package of 80 comics!

Tony Wilsdon
Tony Wilsdon
1 year ago

Hi Brian,
Thanks for the article – it got me to dig out my Reid Fleming comics for a little inventory. Remember me? I was the Saskatooner who chatted with you last year about the works of Dave Geary. Anyhoo, I do have a bunch of the comics, but I particularly treasure a button a girlfriend of mine bought for me in London, England in 1989. The button is from Reid’s favourite TV show, with “Yours truly, IVAN” on it.
I’m a retired high school teacher and I’m proud to say that every time a kid fell asleep in my class (maybe ten times over my career), I’d rouse them with, “Wake up… It’s Christmas… Hey, your Mom’s calling you.” I don’t think any of the kids got the reference, but I hope you get it.

Tony Wilsdon
Tony Wilsdon
1 year ago

Woot! I was just reading through my collection and found an autograph on page one of Eclipse #5!