“Crow” McCay

The Crow McCay Daily Mobster Cartoon Character Design Gangster Nose Trenchcoat black illustration retro turtleneck

“Crow” McCay

Perched up on the telephone pole,

sits a quiet, lonely soul.

Waiting, watching silently,

before swooping down violently.

In this town, there’s no lost-and-found

“Crow” picks up goodies dropped on the ground.

Coins, and jewels that folks may drop,

he can see it all from way up top.

Collecting and scavenging, keeping a stash

then off to the “Crow Bar” to spend his cash.

Just a common thief, a lonely birder,

working alone, avoiding things like murder.

First to the street before the sweepers,

finders keepers, losers weepers.

Illustration Friday: “Lonely”

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Senor Suspendador

Daily Mobster Character Design Cartoon Illustration Cat Burglar Robber Thief Suspenders Hanging Key

Señor Suspendador

Scoot, Scurry, Scramble!

Sue Spence spawns similar swinging swindler!

Sadly, seven souls site scamming situations.

Shoppers suspect shoplifting; some see stealing.

Suspended somewhere, swings Señor Suspendador.

Señor’s sneaky scheme sidesteps security systems.

Señor skips surveillance, skillfully simulating shadows.

Six savings storehouses succumb. Stickup, stickup!

Scared salary savers stampede, silver stockers scream!

Señor skips showily, stashing stolen savings.

Señor Suspendador slights Sue Spence, saying,

“Señor’s scamming surpasses Sue!

Suckers!”

For Illustration Friday’s: Suspend

“Ears” DeRoma

daily_mobster_sketchbookjack_big_ears_deRoma_hat_argyle_character_design_illustration

“Ears” DeRoma

“Ears”, “Ears”, he’ll never impose,

but the more he hears, the more he knows.

Carefully noting every detail,

compiling his list of notes and black mail.

Looking so meek in his argyle vest,

while stashing away all that’s confessed.

He can tell who’s who without turning around,

simply by listening to every sound.

Dumbo and Dopey, he’s heard all the names,

and tired of playing such childish games.

DeRoma is paid quite a handsome fee,

for secrets, gossip, and spying, you see.

So say what you will about his ears and his hat,

but beware, he will hear, far more than that.

“The Box” Burlington

cube box square head bowler hat daily mobster vest bow tie cartoon character design burlington illustration gangster

“The Box” Burlington

Burlington  is the owner of the restaurant on the corner.

No tricky business here, he bought it fair and square;

he was just thinking outside the box, icebox that is.

Everything outside the icebox is legal.

But for the owner of a restaurant, I must say

“Box” is a little rough around the edges.

I can’t say he’s very well rounded,

but don’t get me wrong, he ain’t no square.

Baby Face Morten gets the cubed steak and  The Mayor

loves the linguine squarciarella, the house specialty.

It’s cooking in the kitchen, like ninety degrees hot.

Just don’t get sent to the icebox.

‘Fraidy Freddy

daily mobster sketchbookjack scared paranoid hiding witness worried cartoon character design illustration

‘Fraidy Freddy

‘Fraidy Freddy, always ready

for pop up, criminal plots.

‘Fraidy Freddy, never steady,

flinching at potential shots.

‘Fraidy Freddy, soft and thready,

adjusting his binoculars.

‘Fraidy Freddy, nerves so heady,

watching all passing cars.

‘Fraidy Freddy, sleeps with a Teddy,

and sometimes keeps the light lit.

‘Fraidy Freddy, hiding in bed, he

knows someone’s secret.

‘Fraidy Freddy,  goes by Eddie,

Harold, Murphy and Sam.

‘Fraidy Freddy, a new name already,

in witness protection program.

 

For Illustration Friday: “Secret”

“Sidecar” Sid

sidecar motorcycle biker sid daily mobster sketchbookjack character design illustration cartoon gangster scarf goggles leather jacket bandana

“Sidecar” Sid

He’s the fastest driver that’s ever been,

aiding getaways since nineteen ten.

Fastest thing on four wheels or two,

hold on tight, he’s coming through.

No cars for him, you might think it bizarre,

so you’ll have to ride in the sidecar.

Sid once had to help three thugs flee,

that was quite the sight to see.

Three sidecars all in a daisy chain,

zipping through traffic, lane to lane.

Sid’s plaid scarf was flapping in the wind,

was the last thing they saw before giving in.

“Sidecar” Sid escapes again!

He is driving the coppers totally insane.

But he’s not just a gangster livery,

He also does Chinese delivery!

Lucca “Lucha” Libre

daily mobster sketchbookjack lucca lucha libre luchador cartoon character design illustartion black and white suit tie

Lucca “Lucha” Libre

The masked man strikes again!

Extortion, robberies, and smuggling abound.

No one knows what he really looks like,

not even his mom!

(We know, we interrogated her.)

If you have seen this man, been robbed by this man,

or recently clothes-lined, flying monkeyed, or body slammed,

please contact local authorities immediately.

There has been a rash of sightings and it is unclear

if there is a mob of these men, or just one, changing masks.

Be on the look out for Lucha Libre wrestlers in your neighborhood.

Last seen wearing a white suit, black tie, a fedora

and a luchador mask.

We believe his name is Lucca. Lucca Libre.

Leo Black

The 50th Mobster!

leo black old man daily mobster sketchbookjack character design cartoon illustration gangster hat cigar big nose

Leo Black

(In the style of a 1930s Jim Croce)

Drive in his car, he’ll play the guitar,

sit right back and he’ll sing you a track.

Grumpy, frumpy, old and lumpy,

this big boss is Leo Black.

Shrewd, crude and rather rude,

he controls the land, south of the track.

Joking, smoking, always provoking

everyone from the river and back.

There was a sighting, which incited fighting,

when I got lost and found Mickey Mac.

Chaw was smacking, knuckles cracking,

I said, “Hey, Mac, cut me some slack.”

Mac grinned in the wind, and I was pinned

“Hey, I’m just a kid, and they call me Jack.”

Down on the ground, in the wrong part of town,

I needed something to stop this attack.

Black came out from my car, with my guitar,

Mac looked at him crazy, as he began to unpack.

“What’s with the case, gonna sing us a song?”

The boys came at Black to give him flak.

Then the boys all fled, away from the lead,

shooting from the case, clack clack clack!

Leo Black may be mad and real bad,

I’m just glad Black had my back.

Judge Atticus

judge justice atticus bribe daily mobster cartoon character design illustration sketchbookjack

Judge Atticus

(In the style of Jeremy Irons)

Oh, Judge Atticus, appointed for life.

Must be nice to be free from strife.

Trials in and trials out,

you seemingly judge without a doubt.

But we wonder why mob bosses run free.

Could it be, you’ve taken a fee?

Even when couples come to court to be hitched,

it seems as though you become more enriched.

The gavel comes down on a poor man, blamed.

Yet everyone knows that he’s surely been framed.

They say justice should be objective and blind.

The latter is covered, with glasses of that kind.

But the scales you carry do not weigh facts.

They weigh something green, let’s call it a “tax.”

For Illustration Friday‘s: “Hitched”

Bruce Boxer

bruce the boxer fighter daily mobster sketchbookjack character design illustration cartoon

Bruce Boxer

(In the alliterative key of B)

Boxing buffs, bring big bucks!

Booking bets before boxing bell bangs!

Buy big beers by betting boxes!

Brace before brilliant battles.

Bruce Boxer brawls Big Bad Bart!

Boss Boston bets Bruce Boxer beats Big Bad Bart.

Bam, Boom, Bang, Bop! Bloody, bruising bludgeoning!

Bruce busts Bart’s belly. Bart bangs Bruce’s back.

Bruce bounces back, bashing Bart’s breast.

Bart bounds, besieging below Bruce’s belt.

Bruce bends, broken, but boxing bells bing!

Boss Boston beckons Bruce. Boss binds bricks

between Bruce’s boxing bindings.

Boxing buzzer buzzes!

Bruce boomerangs, backfiring Bart,

bloodying brains, breaking bones.

Bart befalls blackout.

Bruce buries bricks behind back before being barred.

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