Portraiture is one of the oldest forms of art, with a history stretching across millennia and found in nearly all mediums—from painting and drawing to sculpture and photography. While the focus of portraiture for most of art history was capturing the likeness of an individual, the 20th century saw a profound evolution in the genre, and portraiture became a potent site of expression and experimentation. Now live for bidding through March 19, 2025, Artnet Auctions 20th Century Art sale features a range of portraits by some of the century’s leading artists—from Pop artists Andy Warhol and Roy Lichtenstein to Modern masters like Pablo Picasso. Below, we dive into a few of the lots from this sale that highlight the period’s expansive approach to the age-old genre.
Niki de Saint Phalle, Tête de Femme (1982)

Niki de Saint Phalle, Tête de Femme (1982). Est. $30,000–$50,000.
French sculptor Niki de Saint Phalle (1930–2002) rose to prominence through her heavily stylized figuration and employment of an intensely vibrant color palette. Playful and rife with symbolism, Tête de Femme (1982) even includes mobile elements, exemplifying her unique approach to sculptural form, and touching upon themes the artist continually returned to: children, motherhood, and play. This work also marks one of Saint Phalle’s earliest editioned sculptures (a small edition of only seven), which originally hails directly from the Niki Charitable Art Foundation.
Pablo Picasso, Homme au chapeu jouant de la guitare (1914–1915)

Pablo Picasso, Homme au chapeu jouant de la guitare (1914–1915). Est. $80,000–$100,000.
Considered one of the most important artists of the 20th century, Pablo Picasso (1881–1973) contributed to the revitalization and evolution of portraiture. Homme au chapeau jouant de la guitare (1914–1915), a graphite on paper work, or “Man in a hat playing guitar,” features a highly abstract figure holding a guitar, the latter of which is a recurring element across Picasso’s oeuvre. By returning to the form of the guitar, he could craft his abstract visual language more precisely and symbolically touch upon themes of harmony and discord.
Roy Lichtenstein, The Art Critic (1996)

Roy Lichtenstein, The Art Critic (1996). Est. $25,000–$35,000.
With a compositional arrangement referencing Picasso’s Cubist works, and executed using Ben-Day dots, The Art Critic (1996) by Roy Lichtenstein (1923–1997) offers a multilayered view of a woman observing a piece of art. Potentially alluding to the transformative experience of engaging with visual art, another impression of this print is held within the Whitney Museum of American Art in New York.
Michelangelo Pistoletto, Autoritratto col colbacco (1972)

Michelangelo Pistoletto, Autoritratto col colbacco (1972). Est. $10,000–$15,000.
A central figure within the Arte Povera movement, Michelangelo Pistoletto (b. 1933) is best known for his “Mirror Paintings,” which he began in the late 1960s and continues to make today. In a similar mode, Autoritratto col colbacco (1972) is a self-portrait color screenprint applied to mirrored stainless steel, wherein the viewer sees themselves gazing back at the artist, allowing for a mutable, ever-changing composition.

Alex Katz, Ada (1994). Est. $6,000–$8,000.
Alex Katz (b. 1927) is one of the most important American artists of the past century, the subject of hundreds of solo exhibitions across his career, recognized for his distinctive use of flat planes of color and use of figuration. While Katz has turned his creative focus on a wide range of individuals in his work, his wife, Ada, has remained his constant muse, and the subject of more than 250 portraits, such as the present lot.
20th Century Art is now live for bidding through March 19, 2025.