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He Plays the Boss a Dollar a Hole. American cartoon, 1931, by Harold T. Webster featuring his Timid Soul, Caspar Milquetoast
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He Plays the Boss a Dollar a Hole. American cartoon, 1931, by Harold T. Webster featuring his Timid Soul, Caspar Milquetoast
MILQUETOAST: GOLF.
He Plays the Boss a Dollar a Hole. American cartoon, 1931, by Harold T. Webster featuring his Timid Soul, Caspar Milquetoast
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Media ID 7962291
1931 Athlete Caddie Caspar Flag Golf Club Golf Course Golfer Green Harold Player Playing Tucker
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EDITORS COMMENTS
In this classic American cartoon from 1931, artist Harold T. Webster introduces us to the endearing character of Caspar Milquetoast, known for his timid nature and comical misadventures. In "He Plays the Boss a Dollar a Hole" we find Milquetoast on the golf course, engaging in a friendly yet nerve-wracking game with his boss. The scene captures the essence of early 20th-century golfing culture, with its meticulously manicured green and players donning traditional attire. Milquetoast's anxiety is palpable as he tees off, aware that each hole could cost him a dollar if he fails to impress his boss. Webster expertly portrays Milquetoast's inner turmoil through subtle facial expressions and body language. The viewer can almost feel the weight of expectation placed upon our lovable protagonist as he navigates each swing with trepidation. This cartoon not only showcases Webster's artistic talent but also serves as a humorous commentary on workplace dynamics and social anxiety. It reminds us that even in leisurely pursuits like golf, there can be underlying pressures to perform or please those in positions of authority. "He Plays the Boss a Dollar a Hole" remains an enduring piece of American cartoon history, capturing both timeless humor and relatable human experiences. Whether you are an avid golfer or simply appreciate clever storytelling, this print is sure to bring laughter and nostalgia into any space it graces.
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