WHAT IF YOU COULD WATCH THE NEXT GREAT AMERICAN PRESIDENT GROW UP? Jack and Bobby McCallister are two bright young brothers growing up in Hart, Missouri, under the watchful eye of their eccentric single mother Grace, a college professor whose strong personality helps shape both of these young men's lives and secure one a place in the history books - as President of the United States. Grace and Jack's temperamental mother/son relationship takes a dangerous toll on Bobby as he gets caught in their rival forces, prompting a major change in the McCallister household. The arrival of a new college president, Peter Benedict, and his beautiful daughter, Courtney, makes an impression on the McCallisters that lasts a lifetime.
Grace and Bobby help with a College Democrats rally. Jack explodes after catching Grace smoking pot again and gives her an ultimatum. However, after a particularly trying day, Grace seeks refuge in her old habit and is unprepared for the price she must pay for the one joint. One of Grace's co-workers gets fired, and Grace goes to bat for her without all the facts in handCourtney and Jack continue to explore their relationship. Meanwhile, Bobby tries to help make things better for Jack, both with Courtney and in school, but only succeeds in making things worse. Also, it is revealed how President McCallister became affiliated with a surprising political party---Republicans.
Grace goes out of town to a faculty retreat. Bobby joins the ""challenge program"" at school and learns a powerful lesson. Grace is conflicted on what to do when she finds out her student TA plagarized one of her papers in class. Also, Grace is startled by news that Bobby's new teacher gives her regarding Jack. plans a party at the house while Grace is away. Lastly, the flash-forward segments reveal how a surprising ally helps President McCallister out at a critical moment in his political career.
Bobby's interest in religion is piqued when he helps Warren study for his Bar Mitzvah. Elswhere Grace insults a Arab-American female student, Hebba (guest-star Lisa Pintel) with deep religious beliefs. Taking offense, Grace chastises Hebba in front of the class, prompting a campus-wide boycott of her classes. Jack gets a chance to rejoin the track team when the coach needs a replacement runner for Marcus, who's on academic probation. Bobby demands to know why Grace never took him to church. Completely thrown by the accusations, Grace must explain to Bobby & Hebba what ""faith"" really means to her. In the future, pre-President McCallister struggles with his faith.
The future reveals a dark secret about the soon-to-be First Lady. Back in the present, Jack offers to escort a depressed Courtney to her father's work fundraiser leading to an unexpected confession and kiss. Bobby is having problems with another school bully. Meanwhile, much to the consternation of her sons, Grace offers to let a homeless man stay at their house for a few days until she can find him a better place to live.
Grace is stunned after Benedict informs her that her fellow colleague and good friend has been accused of sexually harassing a student. Grace immediately defends her co-worker but must re-think her loyalty when new evidence arises. Meanwhile, Bobby is spending so much time with his new girlfriend, Dex (guest star Jeanette Brox), he begins to neglect his school work. Under pressure from Grace to succeed, Bobby cheats on his test. Still reeling from the guilt of kissing Courtney, Jack is horrified to discover she and Missy (Keri Lynn Pratt) have become friends. Lastly, in the future, President McCallister is accused of sexual harassment.
Bobby's relationship with Dex (guest-star Jeanette Brox) continues to grow until Grace walks in on them kissing in her study. After failing to convince Bobby to break it off with Dex, Grace and Jack take matters into their own hands. Meanwhile, Peter shows his overprotective side when she considers going out with a college frat boy, and though he has Courtney's best interests at heart, ultimately causes her embarrassment among her peers. Also, the future reveals that President McCallister has trouble with his oldest of four sons, Jack, and the secret service.
Bobby is heartbroken over his break-up with Dex (guest-star Jeanette Brox) and decides to get even with Jack after finding out he is responsible for their split. Bobby's actions cause Jack, Missy and Courtney much embarrassment and anger, which results in a feud between the brothers. Bobby accompanies himself on Jack and Missy's date. Meanwhile, Grace and Tom (Bradley Cooper) sneak away from the campus election night party to smoke pot, which proves to be a terrible mistake for Grace and her family. Grace is eagerly awaiting who won the 2004 presidential election. Lastly, in the future 2040 political leaders talk about Pres. McCallister and the night he won the presidential election by only a few votes.
Grace promises to be on her best behavior when she and Jack go to Missy's house for dinner but loses her cool after the Reverend (guest-star Ed Begley, Jr.) starts attacking her ideals poltical policies. Upset by the event, Grace turns to Tom (Bradley Cooper) and the two share a very romantic moment. Meanwhile, Bobby intentionally loses at chess games with Peter in order to spend more time with him. Also, Courtney uses Marcus to get back at Jack. Lastly, in the future Pres. McCallister uses chess in his way of strategizing a war.
Grace's warm, intelligent, gay younger brother Jimmy makes a surprise visit for Thanksgiving. Grace is thrilled that he has returned, but her feelings change after he lands in jail on drug charges. Meanwhile, one of Jack's high school teammates on the track team, Matt, is gay and has a crush on Jack, and is distraught when Jack finds out his reaction. Later on Matt commmits suicide and the whole entire school is surprised by the matter. Jack feels responsible for that matter.
Jack is mortified after Grace catches him buying condoms in reparation for his big night with Missy. Trying to be supportive of his actions, Grace insists that Jack talk to her about sex and questions him about whether he is sure Missy is the right girl. Meanwhile, Jimmy slips back into his old habits, forcing Grace to make a difficult decision about her family. Also, Bobby tries to help Warren win over his crush Deena but is surprised when she declares she has feelings for Bobby.
Jack tries to resume a sense of normalcy after his brutal attack, but finds that the injury may keep him from returning to his old life when he visits the doctor with Grace. Also, Grace accidently runs into one of her students, Natalie, while she is leaving Tom's apartment, but may get busted as she tries to subliminally blackmail Grace with her grade in a later conversation. Meanwhile, Courtney meets a new guy who's tied up in front of her house as a fraternity hazing (guest-star Mike Erwin, ""Everwood""). He captures her interest and tries to get to know him later on. But his feelings for her are not what she had hoped. Lastly, the future reveals President McCallister's unique actions after a horrific bombing in Chicago.
Bobby becomes suspicious of Grace's relationship with Tom after Tom coincidentally shows up during a camping trip and Bobby is not happy at all. While Jack and Missy's relationship seems to be coming to an end as he competes with Truman High's football captain Randy for Missy's affection lately, Courtney's dating life is heating up with college freshman Nate (guest-star Mike Erwin). Also, Jack befriends a girl patient, Katie, who also goes to school with him in the waiting room of his doctor's office for his knee appointment. The future reveals that President McCallister, despite risks involved, supports space travel to the planet Mars.
Jack walks in on Grace and Tom (Bradley Cooper) in a compromising situation and tells Grace he disapproves of her romance. Meanwhile, Bobby convinces Grace to allow him to attend an overnight hunting trip with Peter by blackmailing her on telling Jack about her relationship with Tom before he finds out, which proves to be an eye-opening experience for Bobby. Also, Courtney contemplates moving her relationship with Nate (guest-star Mike Erwin) forward and does this by making him her first sexual experience. Lastly, Jack hangs out with new friend Katie (guest-star Kate Mara) as he adjusts to Missy and Randy (guest-star Cam Gigandet) now coming together.
A bad snow storms hits Hart, Missouri. Grace and Tom's relationship is exposed when a fellow professor catches them kissing in her office. Later in the evening, Peter turns to Grace for advice when he finds out Courtney is having sex with her boyfriend. Meanwhile, Jack's relationship with Katie (guest-star Kate Mara, ""Everwood"") progresses. In an effort to become popular at school, Bobby and Warren (guest-star Dean Collins) decide to have sleep over and come up with a shocking idea to make the evening memorable. Jack, Courtney, Missy and Katie are also trapped together, where they play a game of dare and inevitably leads to Jack and Courtney's first REAL kiss together in front of everyone. Tom babysits Bobby and Warren's sleepover with the ""cool"" kids at Grace's house as he coerced them into coming as they promised they would watch porn. But the plan backfires when the tape goes missing, the power goes out and everyone is trapped. Lastly, Grace and Peter are stuck in their offices on c
Peter is forced to take action after learning about the relationship between Grace and Tom (Bradley Cooper). Grace has to go up against the University Ethics Committee when they find out about her relationship with Tom. Bobby and Warren solicite themselves to members in the neighborhood to do odd jobs, but they keep getting rejected until Mrs. Sorensen has them clean out her infested garage at a very low wage. In a twist, Bobby finds Jack's wallet in the garage that was stolen by one of the guys that robbed him and finds out Mrs. Sorensens godson Ted was storing stuff in his garage. Jack and Marcus decide to confront him where he works, but it doesn't go well. Then, Jack and Marcus immediately call the police but things don't go so well. Marcus and Jack then decide to take matters into their own hands with Ted, but it backfires. In the future Pres. McCallister has to handle being criticized by former Pres. Adler in retaliation to when McCallister criticzed Adler when he was president a
Bobby must research his family history for a school assignment which leads to more unanswered questions about his fathers real life. Jack and Katie's (guest-star Kate Mara) relationship progresses, while Courtney's comes to a screeching halt after Jack discovers Nate (guest-star Mike Erwin) is cheating on her with another girl. Grace and Tom face the reality of their relationship as she is shocked to learn that her affair with Tom has cost her more then she had bargained for. Jack and Katie play a game to see who knows the other better. Neil Patrick Harris guest-stars as a graduate student in the year 2045.
Grace is now working with a new TA, Margaret, which leads Grace at a lost without Tom even with another TA on her side. Grace's excitement to be the opening speaker at an event for her mentor turns to disappointment when she is asked not to speak due to her scandalous relationship with Tom. Grace catches up on old times with a former colleague, Julius Edelman, who was her former mentor when she was a TA at the college. But Grace is a little scared of how he'll feel about her once he finds out about her former relationship with Tom on campus---but the story takes a surprising turn for both. Jack that finds out Bobby is taking a shot a joinging the track team and he instantly shows disapproval. Later, Jack finds out that his relationship with Katie (guest-star Kate Mara) isn't what he thought it was and is shocked to find out that Courtney and Marcus may have feelings for each other.Lastly, Missy joins a Bible Study Group after her break up with Randy, but it doesn't go so well for her.
Missy and Jack go to the school nurse and find out she's pregnant. They eventually tell both their parents and they meet up at the Belknap house to discuss the matter, but does not go well at all with her father, Rev. Belknap (guest-star Ed Begley Jr.) threatening to disown her if she has a child out of wedlock leaving Missy frightened and alone. She eventually goes to an unlikely person, Grace, and both go together to a clinic for a ""procedure."" Bobby decides he wants to go further into religion by wanting to be Baptized and joining the church as he's been taking a few classes and being guided by Rev. Reinhart, but needs a family member to accompany him since he doesn't have a godparent. Rev. Reinhart tries to talk to an uncooperative Grace later on. Bobby is reluctant at the thought of his mom, but eventually Jack and Peter go with him.
After getting into a big argument at the not-so-exciting school dance, Jack, Courtney, Marcus, Missy and Randy (guest-star Cam Gigandet) decide to drive to an after-party, but a deadly car accident prevents them from making it to their destination. They collide with a deer on the road, as Courtney flags down a truck driver as the episode begins and stems back to the hours before the accident. At the end of the episode one of the four are dead, Missy. Meanwhile, Grace agrees to chaperone Bobby's school field trip, much to Bobby's dismay, which proves to be a hurtful and eye-opening experience for Grace. Also, Grace and Bobby sneak into Independence Hall and take a look at an original copy of the ""Declaration of Independence."" Lastly, in the future Pres. Robert McCallister's eldest son, John ""Jack"" McCallister talks about the day his younger 16 year-old brother Henry died in a car accident after driving drunk and his involvement in the matter of his brother's death.
The aftermath of the fatal car accident starts with all the kids' parents meeting up at the hospital to claim their children as well as seeing Missy's parents shatter in grief when they find out about their daughter's death. To protect Marcus, Jack tells the police that he was driving the car the night Missy died. The guilt becomes too much for Marcus and he confesses to his dad, who immediately calls Grace. A surprising ally comes to Jack's aid after Grace demands that he tell the police what really happened. Meanwhile, the group's sadness turns to outrage after Reverend Belknap (guest-star Ed Begley, Jr.) delivers a shocking eulogy at his daughter's funeral. Bobby and Warren say goodbye to each other as Warren moves away promising to stay in touch. In the future we see an adult Warren talk about reuniting with his former best friend, Pres. Bobby McCallister decades later after saying good-bye and never staying in touch with each other since kids. Warren is the most well known success
In the future documentary, there is a host who explains how Jack fought in the War of Americas and became a war hero (but was badly injured with his old knee injury becoming permanent), then became a famous public defender, was elected into Congress, and shot to death by a drug addict while driving to his son's soccer game. Jack was married and had two sons. Bobby was the one who encouraged Jack who was a Democrat to run for Congress and inherited Jack's seat when he died. An older Peter and the Adult Marcus tell what happens after Jack dies. The host also says how everything the brothers do in the future are tied back to the day that they met their father in prison. The future reveals Jack's heartbreaking fate and details Bobby's unlikely road to the Presidency and, for the first time, we hear the voice (Tim Robbins, "Mystic River") of President McCallister. In the present, Jack and Bobby discover that Grace plans to visit their father, Juan (guest star Lou Diamond Phillips, "La Bamba")