The painting depicts a Parisian adolescent boy who holds a pipe in his left hand and wears a garland of flowers on his head, surrounded by two floral decorations.

[1] Preliminary studies for this painting show the boy in a variety of different poses, including standing, sitting, leaning against a wall, lighting a pipe or holding it in his hands.

Picasso eventually chose to depict his model in the seated position shown in the finished painting, which he painstakingly worked on in a preparatory study.

Like Picasso's Young Girl with a Flower Basket, which was painted in the same year, Garçon à la Pipe conveys conflicting imagery of innocence and experience.

It conjures up Verlaine’s poem ‘Crimen Amoris,’ about a palace in Ecbatana where ‘adolescent satans’ neglect the five senses for the seven deadly sins, except for the most handsome of all these evil angels, who is sixteen years old under his wreath of flowers… and who dreams away, his eyes full of fire and tears.Paul von Mendelssohn-Bartholdy probably acquired the painting c.1910.

Shortly before his death in 1935, he wrote a will bequeathing it to his non-Jewish wife, Countess Else Mendelssohn-Bartholdy Kesselstett (née Lavergne-Paguilhen) who sold it to Walter Feilchenfeldt in 1949.

[8][9][4] In 2004, Professor Julius H Schoeps challenged the 1949 sale of Boy with a Pipe due to circumstances related to the Nazi persecution of the Jewish owner and his attempts to shield the painting from seizure via his non-Jewish wife.

In 2004, Charles Moffet, co-director of Impressionist and modern art at Sotheby's remarked on the painting's significance as a masterpiece.It has a haunting ambiguity that has ensured its status as one of Picasso's most celebrated images of adolescent beauty.

[8]Garçon à la Pipe has been described as a masterpiece, yet its sale at auction in 2004 for the price of $104 million caused some controversy amongst art critics.

Picasso expert Pepe Karmel described the work as a "minor painting" and considered that its high sale price showed, "how much the marketplace is divorced from the true values of art".

Blake Gopnik for The Washington Times opined that, "Though the word "masterpiece" was much bandied about in the buildup to the auction, it's unlikely there's a single art historian who would rate this Rose Period picture.