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Description
Xenosimias, as its name ("strange primate") implies, is something of an alien analogue for a monkey. However, as is often the case when drawing analogies between terrestrial and extraterrestrial species, on closer inspection the differences outweigh the similarities.
The first and most fundamental difference between a xenosimian and an earthly primate is their evolutionary histories. As you know, monkeys--and all earthly vertebrates--can trace their ancestry to early chordates. The chordates evolved skulls and spinal chords, paired appendages, jaws, and skeletons made of true bone. One group of fish branched off, developed particularly stout fins, and became tetrapods, a group which would eventually come to include primates.
Things were different for the ancestors of the xenosimians. Even in the earliest fossil forms, they had legs. Whereas monkeys and humans are descended from primitive swimmers, xenosimians are descended from ancient crawlers of the sea floor. These crawlers existed in an abundance of forms, from sprawling mud dwellers to graceful striders of the sea floor, with most groups sporting various combinations of exo- and endoskeletal supports. As their swimming predators grew more powerful, some adapted by growing suits of dermal bone armor. Others took to the open seas themselves, eventually outcompeting many of their former predators. A small minority of forms strengthened their endoskeletal supports and ventured into the shallow reefs and coastal pools of the numerous small landmasses of their world. It was only a matter of time before some began to use their legs to drag themselves onto the shore, like bizarre endoskeletal horsehoe crabs, to lay their eggs in moist burrows, safe from the predators of the sea. It was only a matter of time before some, strengthening their internal skeletons and sealing their skins against moisture loss, decided to stay there. They were the terrestropods.
As this world's vegetation made life on land more hospitable, the terrestropods became ever increasingly adapted to terrestriality. Their limbs adapted relatively quickly to the increased exertion of walking on land, going through a predictable sprawling phase before evolving a more efficient erect gait. Some developed the amniote egg for truly terrestrial reproduction, while the reproductive orifices of others evolved into moist pouches to preserve their eggs and young. The terrestropods underwent an explosion of diversity.
Actually, over a dozen explosions, one for each of the many landmasses of this world. As time went on, tectonic forces brought many of these landmasses together, and thus bringing many of these microcosms of evolution into contact with each other. Competition for niches was fierce, and many unique and extraordinary lineages became extinct.
The ancestors of Xenosimias survives. They specialized, becoming arboreal. Their odd feet became two-pronged graspers. Their blankly alien eyes swiveled to face forward, and their sight grew keen. The posterior extensions of the skeletons, earlier reserved for their reproductive organs, grew into tails.
Tens of millions of years later, one of the products of this line of evolution is the Xenosimias species pictured here. Its vision is fully binocular, its brain large and complex. The four-jawed mouthparts of its ancestors have been modified, with one set of mouthparts becoming flexible graspers, the other strong mandibles for feeding on "insects." Its strange spinal column runs along its ventral surface. Its hairy coat, originally for deterring parasites, is thick and lustrous, making it appear larger to predators and rivals. Its four limbs attach to a single abdominal girdle, and all end in strong, grasping fingers. Its pouch, in which it keeps its eggs and later, its young, is drawn tightly closed at the base of its tail. The tail itself is long and strong, partly a stiff balancing organ, partly a flexible and prehensile fifth limb. Suspended from a tangle of vine-roots, it hungrily eyes a climbing "insect" on a neighboring vine.
The "insect" is actually a relative, a member of a separate lineage of terrestropods. This lineage converged with earthly arthropods, growing small, shelled, and numerous. Its upper pair of mouthparts have extended to become long feelers, while its limbs end in hooked claws, rather than the grasping hands of Xenosimias. These two strange creatures represent just the tiniest glimpse of the wonders of this world.

***

This is the painting I mentioned that I was working on at the end of the description of my "Shadow" painting. As I was working on the Narakan Snapper, the Ribbonlegs, and the various other creatures I was doodling at the time, I came up with the idea of an alien that was sort of like an insect-monkey hybrid. You can see some early ideas for this creature, and the others that I was doodling at that time, in "Moai's Brain": [link] I've been working on this for at least two weeks, only for a short time each day and often not working on it at all for a few days at a time. Not my most efficient painting by any means.
As it usually is for me, the design came first, and the speculative evolution ideas came later. If I'd come up with the evolutionary concept first, the design might have been quite different. Or perhaps not. I'm not sure.
The various features of this creature were inspired by cicadas, marmosets, flies,and Simiosaurs ([link] ). I also looked at a lion's mane a bit when I painted the creature's hair, but it's not obvious. The background was an experiment. Whether it was successful or not, I don't know yet, but I do know that it was fun to paint.

One last thing. This is probably going to be my last involved creature painting for a while. I'll probably still do sketches and the occasional quick thing, like the Shadow, but I'm going to be putting most of my art efforts elsewhere, to practice industrial design, architecture, character design, and so forth. I need to diversify.

EDIT: After getting some critiques from the excellent ProjectHybrid ( [link] ) and kingacer ( [link] ) I've made a few changes. I changed the fur to be darker and somewhat more lustrous, brightened the highlights somewhat on the mandibles, and added some reflection to the eyes, in order to differentiate the different materials and textures. I also added some more detail to the foreground "bug."

Description
Xenosimias, as its name ("strange primate") implies, is something of an alien analogue for a monkey. However, as is often the case when drawing analogies between terrestrial and extraterrestrial species, on closer inspection the differences outweigh the similarities.
The first and most fundamental difference between a xenosimian and an earthly primate is their evolutionary histories. As you know, monkeys--and all earthly vertebrates--can trace their ancestry to early chordates. The chordates evolved skulls and spinal chords, paired appendages, jaws, and skeletons made of true bone. One group of fish branched off, developed particularly stout fins, and became tetrapods, a group which would eventually come to include primates.
Things were different for the ancestors of the xenosimians. Even in the earliest fossil forms, they had legs. Whereas monkeys and humans are descended from primitive swimmers, xenosimians are descended from ancient crawlers of the sea floor. These crawlers existed in an abundance of forms, from sprawling mud dwellers to graceful striders of the sea floor, with most groups sporting various combinations of exo- and endoskeletal supports. As their swimming predators grew more powerful, some adapted by growing suits of dermal bone armor. Others took to the open seas themselves, eventually outcompeting many of their former predators. A small minority of forms strengthened their endoskeletal supports and ventured into the shallow reefs and coastal pools of the numerous small landmasses of their world. It was only a matter of time before some began to use their legs to drag themselves onto the shore, like bizarre endoskeletal horsehoe crabs, to lay their eggs in moist burrows, safe from the predators of the sea. It was only a matter of time before some, strengthening their internal skeletons and sealing their skins against moisture loss, decided to stay there. They were the terrestropods.
As this world's vegetation made life on land more hospitable, the terrestropods became ever increasingly adapted to terrestriality. Their limbs adapted relatively quickly to the increased exertion of walking on land, going through a predictable sprawling phase before evolving a more efficient erect gait. Some developed the amniote egg for truly terrestrial reproduction, while the reproductive orifices of others evolved into moist pouches to preserve their eggs and young. The terrestropods underwent an explosion of diversity.
Actually, over a dozen explosions, one for each of the many landmasses of this world. As time went on, tectonic forces brought many of these landmasses together, and thus bringing many of these microcosms of evolution into contact with each other. Competition for niches was fierce, and many unique and extraordinary lineages became extinct.
The ancestors of Xenosimias survives. They specialized, becoming arboreal. Their odd feet became two-pronged graspers. Their blankly alien eyes swiveled to face forward, and their sight grew keen. The posterior extensions of the skeletons, earlier reserved for their reproductive organs, grew into tails.
Tens of millions of years later, one of the products of this line of evolution is the Xenosimias species pictured here. Its vision is fully binocular, its brain large and complex. The four-jawed mouthparts of its ancestors have been modified, with one set of mouthparts becoming flexible graspers, the other strong mandibles for feeding on "insects." Its strange spinal column runs along its ventral surface. Its hairy coat, originally for deterring parasites, is thick and lustrous, making it appear larger to predators and rivals. Its four limbs attach to a single abdominal girdle, and all end in strong, grasping fingers. Its pouch, in which it keeps its eggs and later, its young, is drawn tightly closed at the base of its tail. The tail itself is long and strong, partly a stiff balancing organ, partly a flexible and prehensile fifth limb. Suspended from a tangle of vine-roots, it hungrily eyes a climbing "insect" on a neighboring vine.
The "insect" is actually a relative, a member of a separate lineage of terrestropods. This lineage converged with earthly arthropods, growing small, shelled, and numerous. Its upper pair of mouthparts have extended to become long feelers, while its limbs end in hooked claws, rather than the grasping hands of Xenosimias. These two strange creatures represent just the tiniest glimpse of the wonders of this world.

***

This is the painting I mentioned that I was working on at the end of the description of my "Shadow" painting. As I was working on the Narakan Snapper, the Ribbonlegs, and the various other creatures I was doodling at the time, I came up with the idea of an alien that was sort of like an insect-monkey hybrid. You can see some early ideas for this creature, and the others that I was doodling at that time, in "Moai's Brain": [link] I've been working on this for at least two weeks, only for a short time each day and often not working on it at all for a few days at a time. Not my most efficient painting by any means.
As it usually is for me, the design came first, and the speculative evolution ideas came later. If I'd come up with the evolutionary concept first, the design might have been quite different. Or perhaps not. I'm not sure.
The various features of this creature were inspired by cicadas, marmosets, flies,and Simiosaurs ([link] ). I also looked at a lion's mane a bit when I painted the creature's hair, but it's not obvious. The background was an experiment. Whether it was successful or not, I don't know yet, but I do know that it was fun to paint.

One last thing. This is probably going to be my last involved creature painting for a while. I'll probably still do sketches and the occasional quick thing, like the Shadow, but I'm going to be putting most of my art efforts elsewhere, to practice industrial design, architecture, character design, and so forth. I need to diversify.

EDIT: After getting some critiques from the excellent ProjectHybrid ( [link] ) and kingacer ( [link] ) I've made a few changes. I changed the fur to be darker and somewhat more lustrous, brightened the highlights somewhat on the mandibles, and added some reflection to the eyes, in order to differentiate the different materials and textures. I also added some more detail to the foreground "bug."