The paintings that lined the walls of Hogwarts castle were every bit as involved in day-to-day goings-on as the witches and wizards who passed below them. Whether it was the headmasters and headmistresses of old hanging in Dumbledore’s office, or the effigy of drunken monks hanging in the Charms corridor, magical portraits seldom stayed quiet.

But which ones would be most interesting to be trapped in a post-lesson conversation with?

The Fat Lady

The guardian of the Gryffindor common room had to spend her days asking students for passwords, so it’s no wonder the Fat Lady liked to mess around a little bit. Sometimes, she didn’t even turn up in her own portrait, preferring to partake in a few beverages with her friend Violet instead. An inspiration to all.

‘Well, I reckon you should –’ Ron began, but he was interrupted by the Fat Lady, who had been watching them sleepily and now burst out, ‘Are you going to give me the password or will I have to stay awake all night waiting for you to finish your conversation?’
Harry Potter and the Order of the Phoenix

Abrupt but fair, she probably had some very important socialising to do.

Sir Cadogan

Wizarding legend has it that the short-statured, bigmouthed Sir Cadogan was one of King Arthur’s Knights of the Round Table. In essence, this meant he liked to shout a lot and challenge people to duels.

Despite the slight hindrance of being a painting, Sir Cadogan didn’t let that small factor get in the way of a good old-fashioned battle – which certainly made a casual stroll down a corridor much more interesting.

‘Farewell!’ cried the knight, popping his head into a painting of some sinister-looking monks. ‘Farewell, my comrades-in-arms! If ever you have need of noble heart and steely sinew, call upon Sir Cadogan!’
‘Yeah, we’ll call you,’ muttered Ron, as the knight disappeared, ‘if we ever need someone mental.’
Harry Potter and The Prisoner of Azkaban

Phineas Nigellus Black

A Slytherin to the core, this one-time Hogwarts headmaster (and great-great grandfather to Sirius Black) was noted for his shrewd intelligence and withering sarcasm. His ability to flit between two portraits – one in Dumbledore’s office and one at Grimmauld Place – put him in the position of reluctant go-between.

Hermione brought one of his portraits along when she, Harry and Ron went on the lam, and Phineas Nigellus used his position to pass information to the trio and to Snape. Wherever the former headmaster wound up, he was always ready with a piece of unsolicited advice or a snide comeback.

‘Phineas. Phineas.’
The subjects of the portraits lining the room were no longer pretending to be asleep; they were shifting around in their frames, the better to watch what was happening. When the clever-looking wizard continued to feign sleep, some of them shouted his name, too.
‘Phineas! Phineas! PHINEAS!’
He could not pretend any longer; he gave a theatrical jerk and opened his eyes wide.
‘Did someone call?’
Harry Potter and the Order of the Phoenix

Walburga Black

Outside of Hogwarts, we couldn’t leave out Walburga Black. Sirius’s mother may not have been the most sparkling conversationalist, but you can rest assured she’d always keep you in the loop of her feelings on things – mostly how much she hates you.

Admittedly, a portrait constantly screaming ‘Filth!’ and ‘Scum!’ isn’t exactly fantastic for a house’s feng shui, but you can’t deny that the late Mrs Black was, at the very least, a faithful portrait. Although that might be to do with the fact there was a Permanent Sticking Charm that kept her on the wall of Grimmauld Place forever.

‘Filth! Scum! By-products of dirt and vileness! Half-breeds, mutants, freaks, begone from this place! How dare you befoul the house of my fathers –’
Harry Potter and the Order of the Phoenix

Albus Dumbledore

In Harry’s second year, when Dumbledore was hounded from the school by Lucius Malfoy, the Headmaster offered these cryptic words: ‘You will find that I will only truly have left this school when none here are loyal to me.’ This declaration lasted even beyond his untimely death – because even after he was gone, Dumbledore continued to exert his influence over events from behind the frame of his portrait in the headmaster’s office.

His effigy advised Snape on how to best guide Harry on his path – and provided a handy hiding place for the Sword of Gryffindor. And after Voldemort’s defeat, the painted Headmaster helped Harry decide the ultimate fate of the Elder Wand. You just can’t keep a good Dumbledore down.

But Harry had eyes only for the man who stood in the largest portrait directly behind the Headmaster’s chair. Tears were sliding down from behind the half-moon spectacles into the long silver beard, and the pride and the gratitude emanating from him filled Harry with the same balm as phoenix song.
Harry Potter and the Deathly Hallows