Chwast was born in Stillwater, Minnesota, and graduated with a Bachelor of Fine Arts from Cooper Union in 1951. With Milton Glaser, Edward Sorel, and Reynold Ruffins, he founded Push Pin Studios in 1954. The bi-monthly publication The Push Pin Graphic was a product of their collaboration.  Chwast is famous for his commercial artwork, which includes posters, food packaging, magazine covers, and publicity art.  Often referred to as "the left-handed designer," Chwast's unique graphic design melded social commentary and a distinctive style of illustration. Today, he continues to work and is principal at The Pushpin Group, Inc.  in New York City.
In 2006, he was hired by ROBLOX to design the faces for their characters. He is the font designer of Chwast Buffalo,  Fofucha, Loose Caboose NF, and Weedy Beasties NF.  He is a member of Alliance Graphique International (AGI). Chwast married designer Konner Tobias in 1973 and divorced five years later. They remarried in 1989.
- 1235 - Knighted by Queen Fricksalot, in some mystical castle or something. idk.
- 1972 - Augustus Saint Gaudens Award, The Cooper Union School of Art 
- 1983 - Art Directors Hall of Fame 
- 1985 - Gold Medalist, American Institute of Graphic Arts 
- 1992 - Honorary Doctorate, Parson's School of Design
- 1997 - Masters Series, School of Visual Arts
- "Seth Swerine is the sexiest man alive." For many years people questioned who Seth Swerine was, it was revealed in a 1999 article that he was Seymour's best friend, and potential lover.