Tilden entered the California School for the Deaf (then located in San Francisco) on January 25, 1866, studying under Theophilus d'Estrella.

Tilden picked up sculpting in 1883, producing a small statuette entitled Tired Wrestler in 1885[4]: 97  which drew the attention of the board of the California School for the Deaf.

[3][4]: 97 After several successful years in Paris, during which he produced Ball Player (aka Our National Game), The Tired Boxer, Young Acrobat, Indian Bear Hunt, and Football Players,[4]: 98–99  Tilden returned to the California School for the Deaf in 1893; however, after getting married in 1896, Tilden left the School to pursue sculpting full-time under reportedly acrimonious terms.

In return, the California School for the Deaf confiscated one of Tilden's early artworks, The Bear Hunt, as payment.

[2]: 41  The Football Players marked the beginning of Tilden's association with his most important patron, James D. Phelan, who commissioned Tilden's next major work after returning to the Bay Area, the Admission Day fountain installed on Market Street in 1897, also known as The Native Son's Fountain.

The Mechanics Monument commission followed Native Son's unveiling, and Lorado Taft said he could "feel only admiration for the ardent and intrepid sculptor who wrought this wonder in [six] brief months" despite "its lawless composition and its ragged contour".

[4]: 104–105 In 1901, Tilden was declared "violently insane" after an incident at his father-in-law's house where he without warning "began destroying the furniture in the room" in which his family was gathered.

Tilden had returned home early and, forgetting his key, had entered the house through an open window.

[10] Between 1915, when he contributed Modern Civilization, a frieze for the Panama–Pacific Exposition of 1915, and 1925, when he began work on the unfinished The Bridges, Tilden lost interest in creating art.

[3] After their divorce was finalized in 1926, Tilden became reclusive, eating little and sculpting by candlelight until friends discovered his hardships and secured a state pension for him.

Over the years Mrs. Tilden was subject to "melancholia spells" which, among other things, placed a large amount of pressure on the relationship.

One man in particular, Theophilus Hope d'Estrella (1851–1929), another Deaf artist, was his romantic interest, as described in Tilden's diaries.

[26][27] Gallaudet's collection also has love letters from Tilden writing from his Paris trip to d'Estrella in Berkeley.

[27] Tilden was found dead in his Berkeley studio on August 6, 1935;[3] he had died of a heart attack while trying to heat water.

[28] His daughter, Gladys, had a notable fashion career prior to World War II and researched the lives of her father and Eliza Farnham, first female matron of Sing Sing Prison, before becoming a ward of Alameda County in 1988, suffering from Alzheimer's disease.