Harvard senior student, Montgomery Kessler (Monty) is in the middle of writing his thesis when his computer suffers hard drive failure and lost all the data stored in it. Monty was able to print a copy of his thesis making it the “sole” copy of his thesis. Afraid that something might happen to it, he sets out in the middle of the night with Courtney (his roommate) to make more copies. Monty trips over a bike rack, breaking his ankle and dropping his thesis on the boiler room of Harvard’s library.
Monty then sneaks into the library with the help of Courtney distracting the guards. He reaches the boiler room only to find a bum reading and burning his thesis page by page. The old man was startled by Monty’s appearance and attacks him. The man introduces himself as Simon B. Wilder, and states that he will be more than happy to give Monty's work back to him, one page at a time, with a price for each page. Monty agrees to it but calls the university police the morning after. He searches Simon’s belongings for his thesis but he was unable to find it.
Simon escapes trial and blames Monty for losing his “home” and blackmails him using his thesis. Monty works for his thesis by giving favours to Simon. This started their friendship and as time passes by, Monty learns some of life’s hard lessons through Simon’s guidance. Simon teaches Monty the importance of using a man’s wisdom and humility in facing life’s problems. Monty’s roommates, Courtney and Everett learned to live with Simon around but Jeffrey is angry that he pays extra for food and worries about the reactions of his parents when they find out all about Simon living there. Jeff turns down Monty’s request to let Simon sleep in the cellar one cold night, leaving Monty no choice but to lie to Simon on why he can’t stay in the attic. Simon sees through Monty’s lies and leaves that night without a word.
On their Christmas break Jeff, Courtney and Everett leaves the house for vacation leaving Monty who’s...