According to the two Lemony Narrators who work in tandem to tell the story, the dramas are all based on Dickens' immensely successful memoirs, which he wrote in prison 20 years later, and which the narrators frequently quote.
Five series and in all 51 episodes were produced between the years 1957 and 1976. The fifth series was more like a sequel series, taking place many years later where a now elderly Dickie discovers that he has an adult son, named Donald D. Doberman.
Both books and audio dramas were translated to several languages, and were hugely popular in both Norway and Sweden. The Norwegian version was even so beloved that Norwegian radio listeners voted it "the best radio crime series ever," and (with the blessings of Rolf and Alexandra Becker) Paul Skoe, who had been the producer of the Norwegian adaptations, wrote two more sequel series (which seem to take place betweeen the fourth and fifth series) where Dickie and his gang visit Norway.
- The Ace: Zig-zagged with Dickie, who is very much presented as The Ace by the Lemony Narrators, who never run out of ways to call him awesome, but his actual dialogue and actions do show that while he is genuinely skilled and intelligent, he's not the infallible mastermind that the narrators constantly push.
- Affably Evil:
- Dickie, especially in the first series (he Took a Level in Kindness in later series). He's a notorious burglar and pickpocket without any scruples, and will occasionally delve into more serious crimes, even murder — in the first series he shoots and kills a number of rival gangsters, though later on he develops a fondness for setting them up so they duke it out and kill each other instead. But apart from this he's charming, polite and friendly to pretty much everyone he meets (when he doesn't play The Gadfly to them), he's loyal to his friends and fiancée, he always keeps his promises and honors his debts, and can be extremely generous when the mood takes him.
- Jim Cooper waivers a bit between this trope and Faux Affably Evil; he's got a nasty temper and has even less scruples than Dickie, but over time he shows himself as quite friendly and even a borderline Reasonable Authority Figure to his gang. It's never quite clear if he's genuine or not — Dickie certainly doesn't think he is.
- Al Capone: Curiously enough, he's not even mentioned even if most of the series takes place in Chicago during his reign. He's mentioned in one episode, in which the respective female presidents of the "Al Capone fan club" and the "Dickie Dick Dickens fan club" argue over whether it's Al Capone or Dickie Dick Dickens who deserves to be known as "the most famous criminal in the world."
- Anti-Hero: Dickie switches between this and Villain Protagonist, but he has enough noble qualities that for the most part he lands on the Anti-Hero side. He may be a thief, a swindler and a cheat, but he's also generous and even kind, and most of his victims are Asshole Victims.
- Anti-Hero Team: Dickie's gang are a classic example. They're amoral thieves and scoundrels who'll readily lie, cheat and steal, but they'll also help out people in need — generally by tricking, robbing and incapacitating the much worse thieves and scoundrels who are threatening said people in need.
- Ascended Extra: Bonco has a fairly minor role in the first series; he was a smalltime crook who by chance got roped into Jim Cooper's gang and at the end of the first series was pressured into luring Dickie into an ambush. He couldn't bring himself to do it, partly because he felt bad and partly because he panicked and revealed the entire plan. After that he instead teamed up with Dickie, and from the second series on he's a trusted member of Dickie's gang and one of the main characters.
- Asshole Victim: Anyone who's seriously harmed by Dickie's antics are generally shown to be terrible people who deserve everything that's coming to them.
- Banana Republic: Canastarica in the third series, a Central American republic where violent revolutions happen around twice a year. Almost by chance, Dickie and his gang end up involved in one of these revolutions, which leads to Dickie being appointed the new President of the republic. He quickly absconds when he learns that the President is always executed come next revolution (and that this was the main reason why his "allies" in the revolution were so eager to give him the position instead of taking it themselves).
- Batman Gambit: One of Dickie's specialties. He's good at predicting how people will react in certain situations, and several of his plans rely on this. Usually the gambits work — but not always. Sometimes there's an unexpected Spanner in the Works, and sometimes it turns out Dickie's miscalculated, either because he didn't have all the info or because he either underestimated or overestimated his opponent.
- Black-and-Gray Morality: Dickie and his gang are thieves, con men and gangsters with no scruples — but they still come across as the good guys because, almost without fail, their antagonists are much worse.
- Brainless Beauty: Effie will occasionally play this role. While she definitely has a brain, and is capable of drawing conclusions, she's got a tendency to Comically Miss the Point, focus on the wrong things, fail to understand obvious hints, and miss obvious connections — mostly so Dickie can explain his plans and reasoning to her in details.
- Cool Old Guy: Opa Crackle. ("Opa" means "Grandpa" in German). His age doesn't hinder him from being the most enthusiastic and gung-ho member of Dickie's gang.
- Damn, It Feels Good to Be a Gangster!: Exaggerated until it becomes parody. While there are a few moments showing that life as a gangster isn't all fun and games, there are many more moments insisting that yes, it is. Dickie himself becomes like an exaggerated hero, with the Lemony Narrators falling over themselves with comically exaggerated praises and descriptions of how awesome he is.
- Deadpan Snarker: Inspector Mackenzie never runs out of sarcasms, a fair few of them directed at Sergeant Martin who isn't always the best at telling when someone's being sarcastic and when they're being sincere.
- Dub Name Change: For some reason, in the Norwegian translation, Bonco has been renamed "Bonzo."
- Early Instalment Weirdness: Dickie is far more ruthless and uncaring in the first series, to the point where he is more a Villain Protagonist than the Anti-Hero he'd quickly be established as. The first series also hasn't quite nailed its cast yet — Bonco and Sergeant Martin do appear, but in much smaller roles than in later series (Sergeant Martin isn't even named and has a notably different personality) and Inspector Mackenzie doesn't appear at all, with the main police adversary being the Small Name, Big Ego Commissioner Hillbilly.
- Faking the Dead: Dickie does this a couple of times, most notably at the end of the first series where he makes it seem like he's been killed in the big shoot-out with Jim Cooper's gang. Made easier by the fact that up until then he's been a Phantom Thief that the police doesn't even have a proper description of, so any of the unidentified bodies could have been him. Jim Cooper is also revealed to have faked his death in the same shoot-out; in the first series it's stated that he was shot and killed while trying to escape — in the fourth series it's revealed that he did escape and laid low in Missouri for a few years.
- Flanderization: Sergeant Martin, in the first series, he sometimes gets loud when he's excited, and when the Commissioner tells him to lower his voice, he does. From the second series on, nothing can get him to lower his voice: he shouts nearly all his lines; he even whispers loudly.
- Fleeting Passionate Hobbies: Leonardo da Cinzano from the final series seems to have a history of these, though only of the creative sort. Several times he mentions some great work of art (like a novel, an opera, a fable, or a painting) that he once started and never got around to finishing because he got busy with something else.
- Green-Eyed Monster: Surprisingly, almost completely averted in Dickie's and Effie's relationship; jealousy doesn't seem to be a thing for them, even on occasions when they would have had good reason so be jealous. It's even subverted on a few occasions.
- In the first series, Dickie discovers that Effie has been "seeing Jim Cooper socially" and is quite angry... but he's not actually that bothered about the prospect of her seeing other men; he's angry because she chose Jim Cooper, who's his arch rival. And his anger fades almost immediately, when he realizes that if she keeps seeing Jim Cooper she can spy for him and report back about any plans Cooper may have.
- In the fifth series, Effie's shocked to discover that Dickie has a son with another woman... but she's not angry that he cheated on her, just mildly annoyed that nobody had told her or Dickie that he'd become a father.
- Good Stepmother: A slightly downplayed version since Donald D. Doberman is already an adult when meeting her, but Effie in the fifth series is arguably a better parent to Donald than Dickie is. Even though she's not his mother, she's 100% supportive and understanding with him, and when Dickie is reluctant to help his newly discovered son out of trouble, Effie is the one who insists they do everything in their power to help poor Donald.
- Guile Hero: Dickie is an Anti-Hero version of this. He prefers to outwit his opponents rather than beat them physically.
- Heterosexual Life-Partners: Donald D. Doberman and Leonardo da Cinzano in the fifth series. They're practically inseparable, except when one of them has been kidnapped and needs to be rescued.
- Iconic Sequel Character: Inspector Lionel Mackenzie is the franchise's most iconic Sympathetic Inspector Antagonist, but he wasn't introduced until a few chapters into the second series.
- I Just Want to Be Normal: Parodied in the first series. Dickie repeatedly insists that he has no ambitions whatsoever and just wants to be a humble pickpocket. He treats it as an annoyance that his rivals keep "forcing" him to pull off bigger and bigger crimes.
- Impossible Theft: Dickie has a knack for these. In the very first episode, learning that Jim Cooper has sicced the police on him, Dickie gets away from the fifty cops pursuing him because, as it turns out, he's stolen all their guns without them noticing. The embarrassed cops call it a day; Dickie dumps the weapons in Lake Michigan.
- Justice by Other Legal Means: Played with. At the end of the first series, Dickie fakes his death and takes on a new identity, having required the papers of a recently-deceased Irish immigrant named Maxim F. Poltingbrook. It's under this identity he marries his fiancée Effie Marconi... and then, a few months later, it turns out the original Maxim F. Poltingbrook was already married, and so Dickie — still under the name Poltingbrook — ends up arrested for bigamy.
- Killed Off for Real: A number of one-shot characters and antagonists end up dead (usually shot), but in general main and recurring characters are safe. The exception is Mummy Tobo-Dutch, who plays an important supporting role in the first series and the early parts of the second series, before she's killed off by James Topper's gang.
- Lemony Narrator: Two of them. They narrate in tandem, are full of exaggerated admiration for Dickie, fill out details and sometimes disagree with each other about which details are unnecessary for the story. In the fifth series they end up arguing so much that one narrator at one point gets fed up, declares that there's no point telling this story, and starts reciting recipes for vegetable stew instead before the other narrator manages to get everything back on track.
- MacGuffin: For the first three series, the gold bars Dickie stole from the Farmer's Bank. They're worth fifty thousand dollars, and everyone wants them, but circumstances keep intervening so that they never actually do anyone any good.
- Mockumentary: The series has traits of this, as the narrators repeatedly insist that it's a dramatization of real events, based on the memoirs written by Dickie Dick Dickens himself.
- Lovable Coward: Bonco is a wimp and a coward, but loyal and genial.
- Neighbourhood-Friendly Gangsters: Dickie's gang, and to some extent Jim Cooper's gang, are generally pleasant enough and avoid unnecessary brutaliry or bloodshed. Other gangs, such as those led by James Topper, Alfonzo Capelli and Admiral Jefferson Harper, are far more ruthless and bloodthirsty.
- Only One Name: Bonco is only ever called "Bonco." Whether this is his first name, his last name, or merely a nickname, is never revealed. In the fourth series, while the gang is crashing a high society party, he is presented as "Achilles von Bonco," but this is probably not his real name.
- Phantom Thief:
- Dickie has traces of this, using trickery, charm and his impossible skills as a pickpocket to reach his goal. It also helps that for much of the series he's mainly known by name and only people in his limited social circles know what he looks like.
- In the final series, Dickie's son Donald D. Doberman is an even clearer example of the trope, being a refined and classy globetrotter and Gentleman Thief with an uncanny ability to be long gone whenever people start wondering where he's at. In his introduction he's even managed to avoid the narrators — they introduce him as being involved in a heist in Toledo, Spain... only to discover that he's not actually there, but has already fled to Baden-Baden, Germany.
- Repetitive Name: Dickie Dick Dickens, of course!
- Small Name, Big Ego: Commissioner Hillbilly in the first series. He's quick to praise his own bravery and determination, but he's not the most competent, nor the most honest, of cops; for most of the series he doesn't really have a clue what's going on and is easily duped.
- Stylistic Suck: Dickie fancies himself a bit of a musician and loves to play the piano, but whenever we hear him play it's immediately obvious that he's not particularly good at it. Even the narrators, usually so eager to exaggerate his virtues and tallents beyond the impossible, can't bring themselves to use bigger words than "not completely without talent" or "mediocre, but enthusiatic" when talking about his playing.
- Suspiciously Similar Substitute: In the first series, Dickie's main police antagonist is the self-glorifying but not particularly competent Commissioner Hillbilly. In the second series, he transfers out of Chicago and is replaced by Inspector Mackenzie, who is both a Suspiciously Similar Substitute and a Foil to Hillbilly. He takes on roughly the same role as Hillbilly, but is a good deal smarter and more competent — where Hilbilly was easily tricked and often didn't realize what was going on before it was too late, Mackenzie is far quicker to suspect foul play, he's fairly good with logical deduction and even occasionally manages to out-maneuver Dickie with some successful Batman Gambits of his own. When he loses in the end it's generally not due to any incompetence on his part, but mostly due to bad luck or some unforeseen Spanner in the Works that Dickie manages to take advantage of. His main flaw is that he's generally too lazy to really put in much effort unless there are some sort of personal stakes for him involved.
- Sympathetic Inspector Antagonist: Inspector Mackenzie quickly reveals himself as this. He's a grouchy, sarcastic and lazy Jerk with a Heart of Gold who ends up with a specific grudge against Dickie because Dickie has outwitted him and made him look like a fool so many rimes... but he's one of the few cops in the series who isn't corrupt or incompetent, and who has a set of moral standards. Even though he complains loudly about having to do his job, when he is on the job he's clever and meticulous and can even become quite the Determinator when he's angry enough. He and Dickie have the odd Enemy Mine moment; at the end of the first of these Mackenzie even laments still having to arrest Dickie after the man has helped him out. (Of course Dickie escapes anyway, so the arrest never happens.)
- Took a Level in Kindness: Could perhaps be chalked up to Early Instalment Weirdness and Characterization Marches On, but Dickie is far more hard-boiled and ruthless in the first series. At a few points he even threatens to kill both Effie and Opa Crackle, something the Dickie from later series would never do.
- Villain Protagonist: As mentioned above, Dickie switches between this and Anti-Hero. He's more Villain Protagonist in the first series, more Anti-Hero in later series.
- What Happened to the Mouse?:
- Dickie's cat Sebastian plays a small but important part in the first series — but is never even mentioned in the second and third series. In the fourth series, Effie complains that "the cat" is playing with a dead mouse in the kitchen, but since this is a few years later, and a different house, it's never specified if this is Sebastian or a different cat.
- In the third series, while in Canastarica, the gang takes in an escaped parrot named Hannibal, which also plays a small but important role in the plot. When they return to the United States at the end of the third series, it's specifically stated that they take Hannibal with them, but he never appears again.
