Monster Character Series

Launch Adobe Illustrator, and draw a Rounded Rectangle. Use the cursor keys before deselecting to give large rounded corners.

Use the Pen Tool to draw a tentacle, starting from the lower body and flowing outwards, avoid any sharp angles otherwise there will be kinks in the tentacles.

Add a really thick stroke to this path, and select the Round Cap option to give rounded eges.

Convert this stroke into a shape by selecting the object and going to Obejct > Expand. De-check the Fill box leaving just the Stroke to be expanded.

Change the black fill to a black outline to match the body for the time being.

Back with the pen tool, draw three more tentacles in differing directions, all originating from roughly the same area of the body.

Expand these strokes and change the outline to match the body. Select the inner two tentacles and copy them before the next step.

Select all five shapes and combine them with the Add To Shape Area Pathfinder Tool, click on the Expand button to reset the shape.

Paste back the tentacles we copied previously by pressing CTRL + F. This will allow us to keep some of the outlines to distinguish the tentacles from the body.

Use the Direct Selection Tool (White Arrow) to delete the lower most points on the tentacles, then move the other points into position further up the body as shown.

Draw a couple of eyes with black ovals from the Circle Tool.

Use the Rounded Rectangle Tool to draw a huge, wide open mouth. Use CTRL + [ to alter the stack and position the mouth behind the tentacles.

Back with the Rounded Rectangle tool draw in two white front teeth.

To delete any overlap from the teeth, copy the mouth shape and paste back into place (CTRL + F). Select this along with one of the teeth and use the Intersect Shape Areas Tool from the Pathfinder Window, click Expand and notice the tooth has been reduced to the outline of the mouth. Paste in the mouth shape again for use with pathfinding the second tooth.

Add a thick black stroke aligned to the outside of the mouth.

Next up we'll create an Uvula (the dangly bit at the back of your mouth). Draw a red circle on the artboard to the side of the monster.
Draw a long vertical Rounded Rectangle, then use the Pen Tool to add a couple of points to the two long edges. Move these inwards with the Direct Selection Tool. Select the Pen Tool again, hold ALT whilst clicking and dragging each of these points to add Bezier Curves. Use the Pen Tool whilst holding ALT to alter the angles of the lower two points to give a smooth flowing line between them.
Select and drag the two middle points upwards and inwards to extend and further enhance the shape.

Centralise these two shapes and use the Substract From Shape Area option from the Pathfinder tool.

Fill the mouth with a deep red, then position the Uvula shape in black to the centre of the mouth.

Go back to the Monster's body and thicken the stroke right up whilst aligning to the outside.

Fill the shape with a monsterish green.

Copy and Paste the body shape back in place, then align the stroke to the inside and change to a slightly darker, more blueish green.

We ideally want the same effect on the two front tentacles, but because these are not complete paths we cannot align the stroke to the inside. Here's how to overcome this.

Copy and paste a tentacle back in place. Select one of the open points with the Pen Tool and close the shape by selecting the opposite open point. You will notice the cursor icon change to indicate the status of the point.

Great, now we can go ahead and add the thick inside stroke, but we are left with the line across the body where the path was just closed.

Select this shape and go to Object > Expand Appearance. This will convert the stroke to a complete shape.

Create a makeshift shape following the contours of the two outlines with the Pen Tool. Use this shape with the Pathfinder Tool to Subtract From Shape Area. You may want to zoom right in and tidy up the points with the Pen Tool and Direct Selection Tool.

Add some finishing touches such as some spots/warts with the Circle Tool. Vary these in size and rotate slightly.

Bring The Slime! The slimey monster wouldn't be complete without some gooey drips, draw a circle, then drag the upper most point upwards with the Direct Selection Tool to create a teardrop shape.
Position these in varying sizes off the ends of the tentacles.

Add a pool of slime by using the Pen Tool, keep the angles loose to give a smooth, flowing shape then send it to the back by pressing CTRL / CMD + [.