Tom loathes going to school and dreads Monday mornings, even to the point of wishing on Mondays that there had been no holiday at the weekend, "it made the going into captivity and fetters again so much more odious." He will attempt to avoid school by any means at his disposal, and the chief reason he envies Huckleberry Finn is that he does not have to go to school.
Although Tom would much rather be outside fishing or swimming, when he does get to school, he generally finds a way to enjoy it. He does this by subverting the purpose of the school and turning it into something that amuses him. We first see him doing this when he begins his affair with Becky Thatcher in chapter 4.
A more typical activity, at the beginning of chapter 7, is joining with his bosom friend Joe Harper in playing with the tick he has captured. Though the games Tom plays in school generally have to be quieter and more furtive than the ones he enjoys at weekends, they are of a similar type and the element of danger in the master's restraining presence may even render them more enjoyable.
The other positive aspect of school, which Tom enjoys but does not acknowledge, is that it gives him a large audience for his clowning and allows him from time to time to play the hero in front of breathless admirers, as he does in chapter 18:
At school the children made so much of him and of Joe, and delivered such eloquent admiration from their eyes, that the two heroes were not long in becoming insufferably "stuck-up." They began to tell their adventures to hungry listeners—but they only began; it was not a thing likely to have an end, with imaginations like theirs to furnish material.
Tom hates school, both Sunday school and ordinary school. As Monday morning rolls around, he has the following thoughts:
Monday morning found Tom Sawyer miserable. Monday morning always found him so—because it began another week’s slow suffering in school. He generally began that day with wishing he had had no intervening holiday, it made the going into captivity and fetters again so much more odious.
School to an active, adventurous boy like Tom, who wants to be outside playing, is "slow suffering" and "captivity." Tom is the opposite of his half-brother, the angelic Sid, who loves school.
Tom pretends to a toothache to try to get out of school, but Aunt Polly pulls his tooth and sends him on his way. En route to school, Tom meets the "romantic" Huck Finn, who, to his envy, is free to play all day. Tom trades him his tooth for the dead cat Huck has found.
As a result, Tom is late, explains to the schoolmaster that it was due to talking to the dread Huck Finn, and gets a beating for his honesty. But none of this is anything compared to the slow, agonizing minutes sitting at a desk waiting for the time to pass. Luckily for Tom, an added penalty is having to sit in the girl's section of the schoolroom, where he gets to flirt with the new student, Becky Thatcher.
In creating a young hero who puts risk taking and active adventuring ahead of book learning, which Tom holds in contempt unless he can read stories about pirates and robbers, Twain continues the American myth building begun by authors such as Washington Irving. Tom is a direct descendant of "The Legend of Sleepy Hollow's" Brom Bones, the red-blooded, practical, socially adept, robust, masculine trickster who might never put his nose in a book but can outwit the scholars any day.
It's fair to say that Tom Sawyer's not really a big fan of school. His whole attitude seems to be that it's crazy to spend all day cooped up inside a schoolhouse being told what to do when there's a big old world outside full of fun and adventure just waiting to be explored. There are just so many better things to do than go to school—climbing trees, swimming, playing pirates—the list is endless. Though still quite a young boy, Tom has already learned a valuable lesson of life, one that's particularly relevant to his view of school: the difference between work and play:
If he had been a great and wise philosopher, like the writer of this book, he would now have comprehended that Work consists of whatever a body is obliged to do, and that Play consists of whatever a body is not obliged to do.
Tom only goes to school when he's obliged to; that's what makes it work, not play. And all work and no play makes Jack a dull boy, as the saying goes. But all play and no work makes Tom Sawyer.
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