Most Iowans know that Samuel Clemens (later known as Mark Twain) lived and worked in Muscatine and Keokuk in the mid-1850s. But few know of his fondness for a precocious Lee County girl while living there.

In July 1855, at age 19, Sam took a boat from Hannibal, Missouri to Keokuk. His brother, Orion, owned the Ben Franklin Book and Job Office downtown. Orion offered Sam work on his largest project to date, the publication of the Keokuk City Directory. The printing office was on the third floor of a four-floor red brick building on Main Street. There was a book store on the ground floor and a music school operated by a Professor Isbell on the second floor. Sam earned $5 a week and free board at Ivins House, perhaps the town’s best hotel.

After his day’s work was finished, Sam would sometimes play the guitar or banjo, and sing comic songs in the print office. Orion and his other apprentices would often join in. Professor Isbell, hearing the ruckus, encouraged Sam and his comrades to enroll in a singing class.

Sam’s outgoing personality, innate gallantry, and dancing skills made him popular. Through Orion’s wife, Mollie, who was close to Sam’s age, and her younger sister, Belle, he met a bevy of girls. In letters, he mentioned his favorites including Ella Patterson and Ella Creel, his own cousin. But one of Orion’s neighbors, “the talented and brilliant” Ann Elizabeth Taylor, was his primary interest.

Ann was born on January 9, 1840 when her family lived at West Point, Iowa. However, they subsequently moved to Ft. Madison and then to Keokuk. Ann’s father, Hawkins Taylor, had been a member of Iowa’s first territorial legislature while at West Point. In the 1850s, he was a Keokuk alderman and was later elected Mayor.

The Taylors’ home was within a block of the Stotts family, with whom Orion Clemens lived during most of 1856, and in the same neighborhood as the Creels and Pattersons. Sam had intimate friends in both families. There is also some evidence the Taylors entertained Sam at their summer property just north of Keokuk, overlooking the Mississippi.

Annie Taylor was well read, musical, liked to draw, and shared Sam’s ability to see the comical side of things. She was something of a rebel, too, having “very irregular” attendance at prayer meetings. She was known to have ambitions beyond marriage, and was attending Iowa Wesleyan College in Mt. Pleasant. Sam’s younger brother, Henry, who also worked at Orion’s print shop, was taken with Annie’s younger sister, Mary Jane.

Sam courted Annie down the locust-lined streets of Keokuk during her school holidays. When she was away at school, they corresponded regularly. Her letters were described as “strikingly original and humorous.” They inspired Sam to write about subjects he knew she, above all others, would appreciate. One of his letters to “My Dear Friend Annie” was about the swarms of bugs attracted by the gas light as he worked late in the printing office at 2 a.m. He imagined a big “president” beetle first buzzing at his flock of lesser insects, and then joining them in church hymns.

Annie once wrote Sam from Iowa Wesleyan about the difficulty of composing a paper. He responded “Ah, Annie, I have a slight horror of writing essays myself. And if I were inclined to write one, I should be afraid to do it, knowing you could do it so much better…” She sent him a drawing of Mt. Pleasant, which he jokingly referred to as “Mt. Unpleasant,” perhaps because the town kept her from his presence.

What is unmistakable in Sam’s letters is his tenderness for Annie Taylor. There was a tone of deference and modesty that might surprise those familiar only with his later writing. When there was a drought in correspondence from Annie, he gently chided her in an attempt to renew the exchanges.

For a time, Sam’s mother, Jane, was concerned that he was headed for marriage while still a pauper. However, the relationship ultimately cooled and Sam appears to have abandoned his efforts to woo Annie. A restless spirit caused him to leave Keokuk after a year and a half. He continued to write his dear friend for a time, but even that correspondence faded.

After attending Iowa Wesleyan for two terms, Annie completed her studies in art and literature at Lindenwood College in St. Charles, Missouri. She was an English instructor there for several years. That was an outstanding accomplishment for a young woman at the time. Annie married Frederick Cunningham, a local man who became postmaster in St. Charles. The two moved to California, where Frederick’s health failed and he died.

Annie came back to the Midwest, marrying Charles A. Cunningham (possibly a relative of Frederick) and setting up a new household in Carrollton, Missouri. The two had no children of their own, but Ann served as a de facto mother to three whom she had educated. During their years in Carrollton, Charles became a judge of the probate court. Ann, however, fell into poor health after age 35. It was said that, in her own home, she was cheerful and a charming conversationalist. However, she was unable to take part in any social life in the town during the last 20 years of her life.

Ann died of pneumonia on January 23, 1916. Her friendship with Sam Clemens had been fleeting and preceded his literary fame. Still, this former Iowan thought enough of Sam to save his letters in a Japanese-style lacquer box for 60 years.

 --John Stuekerjuergen