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Description
I have binge-watched (and subscribed to) a Youtube channel called ExtraCredits (www.youtube.com/user/ExtraCred… ). Specifically, their Extra History videos and Extra Science videos, which inspired me to develop a simplified style to draw historical figures.
As a sort of tribute to them, I took the time to specifically draw some of figures they have covered in their videos.

In no particular order, these represent some of the more famous people throughout history who I could remember off the top of my head. None of them should be too obscure, but I majored in history so... a short description of each just in case you don't know them.
You can probably notice which figures I did first and which last. I kind of liked the progression, the idea that I was getting better as I went on, so I kept it all as it was when I finished each figure.

(From left to right, descending)

Otto von Bismark: Chancellor and principal architect of the Second German Empire, Bismark led a colourful life as a "radical conservative" (a puzzling description, I know), who spearheaded the Kleinedeutsche-model of German unification (excluding the Austrian Empire in favour of Prussia)

Wilhelm II: Emperor of Germany, he led the country during WWI. It didn't end well.

Helmuth von Moltke: Head of the Prussian army during the reign of Wilhelm I, led the united German forces during the Franco-Prussian War against Napoleon III's French Empire. Was one of the first military leaders to innovate around the growing technological advancements in European war.

Paul von Hindenburg: Public face of the German Army during WWI, and arguably de facto ruler of Germany during that time, Hindenburg associated closely with Erich Ludendorff (who while a better military thinker, was less comfortable int he spotlight). Later became Chancellor of Germany (right before silly-'stache took the job)

Adolf Hitler: Yeeeah... what needs to be said, really? Became chancellor, blamed problems on people got those people killed, started the biggest war in history. In the interests of historical objectivity I won't call him a piece of shit.

Erwin Rommel: The Desert Fox himself, a somewhat controversial figure in that his legacy is somewhat questionable. Whilst a general in the Third Reich, the victorious allies treated him like a gentleman-soldier (which in many ways he was), creating what is called the "Rommel Myth". By all accounts a fairly stand-up fellow, he was ordered to commit suicide by Hitler when it was found he may have colluded in the 1944 assassination attempt on Hitler's life.

Walter Model: Another German general who gained a reputation for coming in after the fact to scavenge situations Hitler's micro-managing tended to send into disaster. Committed suicide rather than face soviet "justice".

(Second row)

Cicero: A Roman statesman and lawyer, Cicero was actually not a native Roman, but gained controversy following the dictatorship of Sulla when dealing with a local uprising. Known for his rhetoric and writings, and for opposing (when convenient) Caesar's rise to power.

Caesar: Again, need it be said? Part of the first Triumvirate, a political alliance with military hero, Pompey Magnus, and super-rich Marcus Crassus, Caesar gained hero-status amongst the laity and was loathed by the senatorial class, Caesar conquered Gaul (modern France) before making himself Dictator for Life (which was not legal) of Rome. Murdered by the senate, sparking a civil war that would see the death of the Roman Republic and the birth of the Empire.

Iustinianus: Known in English as Justinian, Emperor of the Eastern Roman Empire, and part of the "last of the Romans" generation. Justinian's reign saw the last mass expansion of Byzantine borders, conflict with the Eastern Sassanian (Sassanid) Empire, failed attempts to unite the Christian church (a doomed project from its inception), and the first recorded mass outbreak of the Black Death.

Theodora: Wife of Justinian, she acted as co-regent and unofficial spymaster, and even ruled in Justinian's stead when he fell into a coma as a result of contracting the plague. Famously shamed the government into standing its ground during the dreaded Nika revolts.

Belisarius: One of the most underrated generals of all-time, Flavius Belisarius was the principle tool by which expansion under Justinian was undertaken, personally retaking North Africa from the Vandals, defeating the Sassanids at the battle of Dara, and almost reconquering Italy from the Ostrogoths.

Vespasian: A criminally underrated Roman Emperor, Vespasian reunited the Empire following the turbulent Year of the Four Emperors, preventing the Empire from fracturing. A fairly modest emperor, Vespasian's principle works were to stabilise the imperial infrastructure and put down rebellions rather than press for personal glory. Saying that, he was responsible for the building of the Flavian Amphitheatre, which we now know as the Colosseum using plunder from his conquests in Judea.
One of my personal favourite Roman Emperors.
Coming of fairly low noble stock, his family were renowned for breeding mules.

Aurelian: By the 200's, the Roman Empire was near utter collapse. Numerous northern tribes invaded, Gaul, Hispania, and Britannia ceded to form the Gallic Empire, and the eastern provinces did ditto to form the Palmyrene Empire. on top of all this, the last of the Severan emperors had been murdered by his own troops, and the previous emperor, Valerian, had been defeated and captured by the Sassanids.
If that wasn't bad enough, Rome was running out of silver so the money was debased and the economy was collapsing.
Who would want to step into this hot mess?
Why, Aurelian did. Reinvigorating the army with the cult of Sol Invictus (the Unconquered Sun), he smashed the northern tribes, captured the Gallic Emperor, Tetricus, and the Palmyrene Queen, Zenobia, and then was promptly murdered.
Good times.

Augustus: Gaius Octavian, nephew of Caesar, later renamed Augustus. Yes, like the month. It was named after this guy. Perhaps one of the most politically astute people ever, Augustus transformed the Roman Republic into the Empire under the quasi-Republican Principate, a system where the structure of the republic was maintained, but where he occupied the position of Princeps (First Citizen), making him the most powerful man in Rome and creating the Julio-Claudian dynasty that would rule until Nero.

(Third row)

Sargon of Akkad: As the name suggests, king of Akkadia. Whilst Sargon has some modern notoriety, he was the emperor of of a Sumerian Empire some 5000 years ago. Intriguingly, his birth story involves being wrapped in a wicker bundle and thrown into a river, only to be found by a drawer of water and later made king. His story tends to share parallels with many biblical legends, but is significantly older.

Hammurabi: First king of the Babylonian Empire, Hammurabi derives a great deal of modern familiarity because of his law code (although his isn't the oldest formal law code we have recorded). His empire pretty much collapsed after his death, but was reinvigorated as the Neo-Babylonian Empire years later.

Akhenaten: Originally Amenhotep, Akhenaten formed one of the world's first monotheistic religions when he scrapped the state pantheon in favour of the Aten (the sun disc, which was not technically a god). He also moved the capital into the middle of the desert for some reason, but after his death the priests of Amun reasserted themselves and tried to erase him from history. It didn't really work very well.

Nefertiti: If not for Cleopatra, Nef would have been the most well-known ancient Egyptian woman of all-time. A reputed beauty, she was the favoured consort of Akhenaten, and is thought to have possibly ruled as queen following his death.

Cyrus the Great: Founder of the Persian Achaemenid Empire, Cyrus even gets a bible mention because of how awesome he was. Created arguably the world's first superpower, his empire was remarkably inclusive and tolerant, and relied upon a system of satraps (sort of client-states) rather than direct central oversight, creating an Empire that lasted until Alexander the Great.

Alexander the Great: Speaking of whom, King of Macedon and Hegemon of the Greek Hegemony, Alexander conquered until that point in time the world's largest Empire. Before he was 23. I mean, DAMN! He did like to emulate the Persians a bit though, which his men disliked.
He promptly died of poison/health complication/drinking, could have been any of them, and his empire instantly fractured into the Macedonian, Ptolomaic, Seleucid, and Baktrian Empires (amongst some other successor states).

Hannibal Barca: The SCOURGE of Rome, the man whom Roman mothers whispered scary stories of to their children at night. Instigated the second Punic War with the Roman Republic which, ultimately, led to Roman domination of the Mediterranean. Before that though, he crushed the Romans a number of times, and used a now-extinct species of African elephant in his campaigns.

Catherine the Great: Or, all-wise-mother-of-the-fatherland. Yes, that was almost her title, as voted during a general assembly. Overthrew her arguably incompetent husband, Peter III, and rued as sovereign autocrat of the Russian Empire during one of its most successful periods. Transformed the Russian military into a first-class force under the leadership of her lover, Potemkin, instituted social reforms, secularised the Orthodox church, and introduced innoculation to Russia by personal example.
You hear that, anti-vaxxers? They've been doing it since the 18th century.

Frederick the Great: Actually, "the Great" does not do this guy justice. King of Prussia through the War of Austrian Succession and the Seven Years War (the first truly world war), Old Fritz as he came to be known transformed Prussia from a second-rate power to a power to rival the Hapsburgs themselves.
Forgotten in recent years cuz the nazis. Fucking nazis.

Maria Theresa: The Hapsburg whom was the subject of the aforementioned War of Austrian Succession. When her father Charles VI died, she inherited the Austrian throne by virtue of the Pragmatic Sanction of 1713 (which I wrote a paper on), but Fritz countered "Objection!" by quoting Salic law which precluded female inheritance, thus allowing him to begin the war and take the region of Silesia.
She never, ever forgave him for that. Ever.

Robert Walpole: Did something sneaky happen in the 18th century? It was probably Walpole. Riding to power as the first ever Prime Minister of Great Britain on the catastrophe that was the South Sea Bubble (a financial scandal that puts Enron to utter shame), he used the situation to remove everyone opposing him from power (especially those in his own Whig party.)

Arthur Wellesley: The Duke of Wellington himself, the man who finally trounced Napoleon. A national hero and object of worship up until the days of WWI, the duke embodied everything that was British. Despite being Irish.

Napoleon: First Emperor of the French, namesake of the Napoleonic Wars, and victor of the Wars of the first, second, third, fourth, and fifth coalitions. Reached his peek around about the Battle of Austerlitz, after which he invaded Russia. Needless to say it didn't end well. He was banished to an island off of Italy, escaped, was defeated again, and then banished again to the middle of the Atlantic where he later died.

William Gladstone: One of the principle figures of the now defunct Liberal Party of Britain. He gained a reputation of odd virtue for a politician of the age, allegedly making the rounds in London with his wife to find prostitutes. To help them, I mean, get them on their feet and become respectable and whatnot. What were you thinking about?

Benjamin Disraeli: Prime Minister under Queen Victoria. A master of foreign policy to rival Bismark, he gained the title of Lord Beaconsfield in exchange for making the Queen the Empress of India.

Neville Chamberlain: Poor chap. Considered a weak-willed push-over today, he's most well-known for signing a peace agreement with Hitler to ensure peace between the Third Reich and the British Empire by gaining a promise from Hitler that he wouldn't invade Poland.
Hitler promptly invaded Poland, and Britain went to war. Chamberlain died in office amid general head-shaking.

Description
I have binge-watched (and subscribed to) a Youtube channel called ExtraCredits (www.youtube.com/user/ExtraCred… ). Specifically, their Extra History videos and Extra Science videos, which inspired me to develop a simplified style to draw historical figures.
As a sort of tribute to them, I took the time to specifically draw some of figures they have covered in their videos.

In no particular order, these represent some of the more famous people throughout history who I could remember off the top of my head. None of them should be too obscure, but I majored in history so... a short description of each just in case you don't know them.
You can probably notice which figures I did first and which last. I kind of liked the progression, the idea that I was getting better as I went on, so I kept it all as it was when I finished each figure.

(From left to right, descending)

Otto von Bismark: Chancellor and principal architect of the Second German Empire, Bismark led a colourful life as a "radical conservative" (a puzzling description, I know), who spearheaded the Kleinedeutsche-model of German unification (excluding the Austrian Empire in favour of Prussia)

Wilhelm II: Emperor of Germany, he led the country during WWI. It didn't end well.

Helmuth von Moltke: Head of the Prussian army during the reign of Wilhelm I, led the united German forces during the Franco-Prussian War against Napoleon III's French Empire. Was one of the first military leaders to innovate around the growing technological advancements in European war.

Paul von Hindenburg: Public face of the German Army during WWI, and arguably de facto ruler of Germany during that time, Hindenburg associated closely with Erich Ludendorff (who while a better military thinker, was less comfortable int he spotlight). Later became Chancellor of Germany (right before silly-'stache took the job)

Adolf Hitler: Yeeeah... what needs to be said, really? Became chancellor, blamed problems on people got those people killed, started the biggest war in history. In the interests of historical objectivity I won't call him a piece of shit.

Erwin Rommel: The Desert Fox himself, a somewhat controversial figure in that his legacy is somewhat questionable. Whilst a general in the Third Reich, the victorious allies treated him like a gentleman-soldier (which in many ways he was), creating what is called the "Rommel Myth". By all accounts a fairly stand-up fellow, he was ordered to commit suicide by Hitler when it was found he may have colluded in the 1944 assassination attempt on Hitler's life.

Walter Model: Another German general who gained a reputation for coming in after the fact to scavenge situations Hitler's micro-managing tended to send into disaster. Committed suicide rather than face soviet "justice".

(Second row)

Cicero: A Roman statesman and lawyer, Cicero was actually not a native Roman, but gained controversy following the dictatorship of Sulla when dealing with a local uprising. Known for his rhetoric and writings, and for opposing (when convenient) Caesar's rise to power.

Caesar: Again, need it be said? Part of the first Triumvirate, a political alliance with military hero, Pompey Magnus, and super-rich Marcus Crassus, Caesar gained hero-status amongst the laity and was loathed by the senatorial class, Caesar conquered Gaul (modern France) before making himself Dictator for Life (which was not legal) of Rome. Murdered by the senate, sparking a civil war that would see the death of the Roman Republic and the birth of the Empire.

Iustinianus: Known in English as Justinian, Emperor of the Eastern Roman Empire, and part of the "last of the Romans" generation. Justinian's reign saw the last mass expansion of Byzantine borders, conflict with the Eastern Sassanian (Sassanid) Empire, failed attempts to unite the Christian church (a doomed project from its inception), and the first recorded mass outbreak of the Black Death.

Theodora: Wife of Justinian, she acted as co-regent and unofficial spymaster, and even ruled in Justinian's stead when he fell into a coma as a result of contracting the plague. Famously shamed the government into standing its ground during the dreaded Nika revolts.

Belisarius: One of the most underrated generals of all-time, Flavius Belisarius was the principle tool by which expansion under Justinian was undertaken, personally retaking North Africa from the Vandals, defeating the Sassanids at the battle of Dara, and almost reconquering Italy from the Ostrogoths.

Vespasian: A criminally underrated Roman Emperor, Vespasian reunited the Empire following the turbulent Year of the Four Emperors, preventing the Empire from fracturing. A fairly modest emperor, Vespasian's principle works were to stabilise the imperial infrastructure and put down rebellions rather than press for personal glory. Saying that, he was responsible for the building of the Flavian Amphitheatre, which we now know as the Colosseum using plunder from his conquests in Judea.
One of my personal favourite Roman Emperors.
Coming of fairly low noble stock, his family were renowned for breeding mules.

Aurelian: By the 200's, the Roman Empire was near utter collapse. Numerous northern tribes invaded, Gaul, Hispania, and Britannia ceded to form the Gallic Empire, and the eastern provinces did ditto to form the Palmyrene Empire. on top of all this, the last of the Severan emperors had been murdered by his own troops, and the previous emperor, Valerian, had been defeated and captured by the Sassanids.
If that wasn't bad enough, Rome was running out of silver so the money was debased and the economy was collapsing.
Who would want to step into this hot mess?
Why, Aurelian did. Reinvigorating the army with the cult of Sol Invictus (the Unconquered Sun), he smashed the northern tribes, captured the Gallic Emperor, Tetricus, and the Palmyrene Queen, Zenobia, and then was promptly murdered.
Good times.

Augustus: Gaius Octavian, nephew of Caesar, later renamed Augustus. Yes, like the month. It was named after this guy. Perhaps one of the most politically astute people ever, Augustus transformed the Roman Republic into the Empire under the quasi-Republican Principate, a system where the structure of the republic was maintained, but where he occupied the position of Princeps (First Citizen), making him the most powerful man in Rome and creating the Julio-Claudian dynasty that would rule until Nero.

(Third row)

Sargon of Akkad: As the name suggests, king of Akkadia. Whilst Sargon has some modern notoriety, he was the emperor of of a Sumerian Empire some 5000 years ago. Intriguingly, his birth story involves being wrapped in a wicker bundle and thrown into a river, only to be found by a drawer of water and later made king. His story tends to share parallels with many biblical legends, but is significantly older.

Hammurabi: First king of the Babylonian Empire, Hammurabi derives a great deal of modern familiarity because of his law code (although his isn't the oldest formal law code we have recorded). His empire pretty much collapsed after his death, but was reinvigorated as the Neo-Babylonian Empire years later.

Akhenaten: Originally Amenhotep, Akhenaten formed one of the world's first monotheistic religions when he scrapped the state pantheon in favour of the Aten (the sun disc, which was not technically a god). He also moved the capital into the middle of the desert for some reason, but after his death the priests of Amun reasserted themselves and tried to erase him from history. It didn't really work very well.

Nefertiti: If not for Cleopatra, Nef would have been the most well-known ancient Egyptian woman of all-time. A reputed beauty, she was the favoured consort of Akhenaten, and is thought to have possibly ruled as queen following his death.

Cyrus the Great: Founder of the Persian Achaemenid Empire, Cyrus even gets a bible mention because of how awesome he was. Created arguably the world's first superpower, his empire was remarkably inclusive and tolerant, and relied upon a system of satraps (sort of client-states) rather than direct central oversight, creating an Empire that lasted until Alexander the Great.

Alexander the Great: Speaking of whom, King of Macedon and Hegemon of the Greek Hegemony, Alexander conquered until that point in time the world's largest Empire. Before he was 23. I mean, DAMN! He did like to emulate the Persians a bit though, which his men disliked.
He promptly died of poison/health complication/drinking, could have been any of them, and his empire instantly fractured into the Macedonian, Ptolomaic, Seleucid, and Baktrian Empires (amongst some other successor states).

Hannibal Barca: The SCOURGE of Rome, the man whom Roman mothers whispered scary stories of to their children at night. Instigated the second Punic War with the Roman Republic which, ultimately, led to Roman domination of the Mediterranean. Before that though, he crushed the Romans a number of times, and used a now-extinct species of African elephant in his campaigns.

Catherine the Great: Or, all-wise-mother-of-the-fatherland. Yes, that was almost her title, as voted during a general assembly. Overthrew her arguably incompetent husband, Peter III, and rued as sovereign autocrat of the Russian Empire during one of its most successful periods. Transformed the Russian military into a first-class force under the leadership of her lover, Potemkin, instituted social reforms, secularised the Orthodox church, and introduced innoculation to Russia by personal example.
You hear that, anti-vaxxers? They've been doing it since the 18th century.

Frederick the Great: Actually, "the Great" does not do this guy justice. King of Prussia through the War of Austrian Succession and the Seven Years War (the first truly world war), Old Fritz as he came to be known transformed Prussia from a second-rate power to a power to rival the Hapsburgs themselves.
Forgotten in recent years cuz the nazis. Fucking nazis.

Maria Theresa: The Hapsburg whom was the subject of the aforementioned War of Austrian Succession. When her father Charles VI died, she inherited the Austrian throne by virtue of the Pragmatic Sanction of 1713 (which I wrote a paper on), but Fritz countered "Objection!" by quoting Salic law which precluded female inheritance, thus allowing him to begin the war and take the region of Silesia.
She never, ever forgave him for that. Ever.

Robert Walpole: Did something sneaky happen in the 18th century? It was probably Walpole. Riding to power as the first ever Prime Minister of Great Britain on the catastrophe that was the South Sea Bubble (a financial scandal that puts Enron to utter shame), he used the situation to remove everyone opposing him from power (especially those in his own Whig party.)

Arthur Wellesley: The Duke of Wellington himself, the man who finally trounced Napoleon. A national hero and object of worship up until the days of WWI, the duke embodied everything that was British. Despite being Irish.

Napoleon: First Emperor of the French, namesake of the Napoleonic Wars, and victor of the Wars of the first, second, third, fourth, and fifth coalitions. Reached his peek around about the Battle of Austerlitz, after which he invaded Russia. Needless to say it didn't end well. He was banished to an island off of Italy, escaped, was defeated again, and then banished again to the middle of the Atlantic where he later died.

William Gladstone: One of the principle figures of the now defunct Liberal Party of Britain. He gained a reputation of odd virtue for a politician of the age, allegedly making the rounds in London with his wife to find prostitutes. To help them, I mean, get them on their feet and become respectable and whatnot. What were you thinking about?

Benjamin Disraeli: Prime Minister under Queen Victoria. A master of foreign policy to rival Bismark, he gained the title of Lord Beaconsfield in exchange for making the Queen the Empress of India.

Neville Chamberlain: Poor chap. Considered a weak-willed push-over today, he's most well-known for signing a peace agreement with Hitler to ensure peace between the Third Reich and the British Empire by gaining a promise from Hitler that he wouldn't invade Poland.
Hitler promptly invaded Poland, and Britain went to war. Chamberlain died in office amid general head-shaking.