Quiz: Cindy Sherman vs The Old Masters

Magda Michalska, Aniela Rybak-Vaganay 24 March 2022 min Read

Time for a little quiz for all those who consider themselves experts in the Old Masters! We will show you photographs made by Cindy Sherman, a contemporary American photographer, which reference famous portraits from art history. See how many of the inspirations in Cindy Sherman’s Old Masters photos you can guess. 

1. Untitled #224, 1990

cindy sherman old masters
Cindy Sherman, Untitled #224, 1990, Museum of Modern Art, New York, NY, USA.

Cindy Sherman’s photographs focus on inventing personas or tableaus that examine the construction of identity, the nature of representation (especially female!), and the artifice of photography.

2. Untitled #216, 1989

cindy sherman old masters
Cindy Sherman, Untitled #216, 1989, Museum of Modern Art, New York, NY, USA.

Sherman always prepares her images from scratch as she assumes the multiple roles of photographer, model, makeup artist, hairdresser, and stylist.

3. Untitled #205, 1989

cindy sherman old masters
Cindy Sherman, Untitled #205, 1989, Museum of Modern Art, New York, NY, USA.

Sherman works in series, with each being self-contained and internally coherent, but all of them are at the same time connected by recurring themes such as the grotesque, the mythical, or gender and class identity.

4. Untitled #228, 1990

Cindy Sherman old masters
Cindy Sherman, Untitled #205, 1989, Museum of Modern Art, New York, NY, USA.

Her History Portrait or Old Masters series of 35 photographs blend postmodern consciousness with timeless masterpieces (or the tropes that they represent) of European masters. Cindy Sherman’s Old Masters series was created during the years 1989 and 1990 while she was living in Rome, but as she recalled:

When I was doing those history pictures I was living in Rome but never went to the churches and museums there. I worked out of books, with reproductions.

Cindy Sherman, quoted in Michael Kimmelman, “AT THE MET WITH: Cindy Sherman; Portraitist In the Halls Of Her Artistic Ancestors“, New York Times, 19 May 1995.

Is this why they all bear a disquieting quality? For their open artificiality and unsettling use of props?


1. Caravaggio, Sick Young Bacchus

cindy sherman old masters
Caravaggio, Sick Young Bacchus, 1593, Galleria Borghese, Rome, Italy.

The first inspiration behind Sherman’s photograph was (we hope you guessed!) Sick Young Bacchus by Caravaggio. This painting is believed to be an early self-portrait of the artist. It was most likely painted around the time when Caravaggio arrived in Rome and then spent six months in a hospital. There are various hypotheses on which illness was depicted here. The painting has been analyzed by many health specialists, who suspect malaria or anemia.

Apart from this, the artwork was an excellent advertisement for the artist as it is a portrait, and also includes elements of still-life. A perfect sample of Caravaggio’s work!

2. Jean Fouquet, Virgin and Child Surrounded by Angels

Jean Fouquet, Virgin and Child Surrounded by Angels, right wing of the Melun Diptych, Royal Museum of Fine Arts, Antwerp, Belgium.

The second photo comes from the right wing of the Melun Diptych, one of the strangest depictions of the Virgin Mary in art history. Sherman perfectly mirrors the strange, round, almost Cubist breast. However, she didn’t represent the unusual red and blue cherubs from the background.

3. Raphael, La Fornarina

cindy sherman old masters
Raphael, La Fornarina, 1518-1520, Galleria Nazionale d’Arte Antica, Rome, Italy.

Another masterpiece from Cindy Sherman’s Old Masters series is La Fornarina. A painting by a master of High RenaissanceRaphael. This portrait stayed in the artist’s studio until the day of his death. Maybe it was a picture of his lover? Some believe it could be Margarita Luti, a woman whom Raphael wanted to marry, but she refused.

4. Sandro Botticelli, Judith Leaving the Tent of Holofernes

Sandro Botticelli, Judith Leaving the Tent of Holofernes, 1495-1500, Rijksmuseum, Amsterdam, Netherlands.

The last of Sherman’s artworks (how many did you manage to guess?) is modeled on Judith Leaving the Tent of Holofernes by Botticelli. It is a popular biblical story depicted by many artists throughout centuries. Judith, a young Jewish widow, decided to save her people from their enemy – King Holofernes of Assyria. She pretended to be attracted to the man and offered herself as his lover in order to behead him while he slept, saving her people from the Assyrian reign. In this depiction of the subject, we see Judith leaving Holofernes’ tent with his severed head.

Did you recognize all the paintings that inspired Cindy Sherman’s Old Masters photographs?

Get your daily dose of art

Click and follow us on Google News to stay updated all the time



The Enneagram Types in Art – Of Amazing Painters, Paintings and Diagrams

If you are anything like us, your social media feed is probably full of quizzes! From “What is your ideal decorating style?” to “What is your...

Ledys Chemin, Giordana Goretti 15 January 2024


Seven Errors Game with Lucas Cranach the Elder

Do you like games? Your mission in today’s game is to identify seven differences between the artworks of Lucas Cranach the Elder that I chose...

Rute Ferreira 22 June 2018