Gainsborough and Co.’s Best Portraits

As I was flipping through some of my art history materials lately, I came upon a realization: British portraits of the late 18th century are actually some of the most entertaining things ever. Why? Well, around that time, Neoclassicism and Romanticism began to take root in Great Britain, and painters continued to create portraits of their wealthy clients in the styles of the day. The true masters of British portraiture in the late 1700s were Thomas Gainsborough and Joshua Reynolds, both featured in the Art Docent Program’s curriculum. So of course most of the portraits created in that time period are pretty distinguished–excepting these few. The facial expressions of the sitters really make their personality stand out. Even the masters of portraiture of the time had a few paintings featuring what seem to be more eccentric sitters. So here are, in my opinion, some of the most entertaining portraits by British artists of the late 20th century.


1. Karl Friedrich AbelThomas Gainsborough, ca. 1777. “Seriously, you couldn’t have picked a worse time to paint me, guys.”

“Was this really the best time for this?” c/o wikimedia.


2. Margaret Cocks, later Margaret Smith. Richard Cosway, 1787. When you read the same paragraph 5 times because you can’t focus.


Or “did I leave the iron on?” Inset c/o


3. Young Hobbinol and Ganderetta. Thomas Gainsborough, c. 1788. Child on right: “Please move along this doesn’t concern you.”

Really. Move along now. c/o


4. Sarah (Kemble) Siddons as the Tragic Muse. Joshua Reynolds, 1783-1784. “Let me think really hard about how much I care.”

“The allegories behind me say I don’t care. At all.” c/o



5. Penelope (Pitt), Viscountess Ligonier.  Thomas Gainsborough, 1770. Few people in the history of art could match Ms. Pitt’s sass level in this painting.

Sass level: 110%. c/o


6. Mr. and Mrs. Andrews. Thomas Gainsborough, 1750. “You can’t sit with us.”

“And we only wear jeans or track pants on Fridays.” c/o


7. Dr. Isaac Schomberg. Thomas Hudson, ca. 1750-1760. “No I’m not uncomfortable, why would you say that?”

“Seriously guys, I’m fine. This doesnt make me anxious at all.” c/o



8. Colonel Acland and Lord Sydney: The Archers. Joshua Reynolds, 1769-1770. Guy in front doesn’t know what he’s doing. Guy behind him is way too enthusiastic about it.

“Yes, of course I’ve strung a bow before. Do I look like an amateur to you? On second thought, don’t answer that.” c/o


9. Jane Fleming, later Countess of Harrington.  Joshua Reynolds, c. 1778-1779. “I woke up like this.”

#flawless. c/o



10. Two Boys by Candlelight, Blowing a Bladder. Joseph Wright of Derby, c. 1767-1773. I’m not even sure where to begin with this one. Blowing pig bladders up and playing with them like a balloon was a common source of entertainment for children (they do so in Little House on the Prairie), but I still don’t see why we need a painting about it.

Why. c/o



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