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Season 1

1 :01x01 - Pilot

Sep/12/2004
Jack and Bobby McCallister are two brothers being raised in Hart, Missouri by their eccentric single mother Grace, a college professor. Grace's strong personality and beliefs are instilled in both of the boy's lives, leading one of which to become President of the United States. The Benedict family, Peter and his daughter Courtney, move to Hart, and they both have an impact on the McCallister's lives.
Guest Stars: Dakin Matthews as Merle Horstadt | Nick Krause as Bully in Rich's Posse | Brenda Wehle as Adult Courtney McCallister | Amber Heard as Liz | Charles Sanders as Principal Farber | Kit Gwin as Miss Murphy | Glenn Powell, Jr. as Rich Wolf | Preston Jones as Nick | Angela Rawna as Nurse | Dean Collins as Warren Feide | Ron Canada as Adult Marcus Ride | John Aylward as Victor Sable | Tess Harper as Former Vice President Karen Carmichael | Ash Christian as Justin |
Uncredited: David Paymer as Adam Chasen
Director: David Nutter

2 :01x02 - Better Days

Sep/19/2004
Grace, with the help of Bobby, organizes and leads a Democrat rally for the college students. Jack catches Grace smoking pot again, and becomes enraged. Meanwhile, Jack and Courtney's budding relationship continues to grow, and we see how President McCallister became affiliated with a surprising political party -- Republican.
Guest Stars: John Heard as Dennis Morgenthal | Nancy Lenehan as School Secretary | Brooke Bloom as Bridget | Charles Sanders as Principal Vincent Farber | Brenda Wehle as Adult Courtney McCallister | Ron Canada as Adult Marcus Ride | Vernee Watson-Johnson as Vera Vaughn |
Co-Guest Stars: Billy Briggs (1) as Student #1 | Joyce Fessides as Cafeteria Lady
Director: Mick Jackson
Songs: John Hiatt -- Have A Little Faith In Me

3 :01x03 - The Kindness of Strangers

Sep/26/2004
While Grace is out of town for a faculty retreat, Jack plans a big party at the house. At school, Bobby learns a life lesson after he joins the "challange program". Meanwhile, Grace finds out that her graduate TA plagerized one of her papers, and is torn between how to approach the problem. Also, flash-forwarding to the McCallister presidency shows a critical move in the President's career.
Guest Stars: Kyle Patrick as The Random Guy | Nelson Mashita as Mr. Chou | Luis Avalos as Mr. Luis | John Heard as Dennis Morgenthal | Alex D. Linz as Hunter | Amy Sloan as Tammy | Hosea Chanchez as Some Random Drunk | David Henrie as The Sniffly Kid | Dakin Matthews as Merle horstadt | Ron Canada as Marcus Ride (adult) | David Paymer as Adam Chasen | Paul Sorvino as President Lorio | Brock Cuchna as Coop | Bennet Guillory as George
Director: David Nutter

4 :01x04 - A Man of Faith

Oct/03/2004
Warren has to study for his upcoming Bar Mitzvah and after Bobby helps him, he becomes interested in religion. Grace's class is boycotted after she insults an Arab-American student, then chastises her in front of the class. Later, Grace has to explain how she feels about religion to both Bobby and the Arab-American student. Meanwhile, Jack rejoins the track team as a replacement for Marcus.
Guest Stars: Barbara Eve Harris as High School Teacher | Pamela Roylance as Mrs. Evelyn Belknap | Rich Ceraulo as Bryce | Harris Laskaway as Rabbi Rosinski | Lina Patel as Hebba Narjali | William C. Mitchell as Rabbi | Jeffrey D. Sams as Track Coach | Ed Begley, Jr. as Rev. Belknap | Ron Canada as Marcus Ride (adult) | Dean Collins as Warren Feide | Thom Gossom, Jr. as Mr. Ride | T.J. Thyne as Todd Shotz
Director: Peter Markle

5 :01x05 - The First Lady

Oct/10/2004
Jack takes Courtney to a fundraiser put on by her father. The night leads to a surprise confession and a kiss. At school, Bobby has trouble with a bully, but soon finds a way to deal with him. Meanwhile, Grace invites a homeless man to stay at the McCallister's house until he finds something more permanent. In a flash-forward to the future, a secret about the future First Lady is revealed.
Guest Stars: John Dennis Johnston (1) as Jonah Babbage | Amy Watt as Deborah Finch | Chad Everett as Mr. Henry 'Huck' Graham | Erik M. Walker as Crew Member #1 | Mary Gordon Murray as Martha Truggman | Jeanette Brox as Dex Truggman | Dean Collins as Warren Feide | Joel McKinnon Miller as Officer Marty Shallock
Director: David Petrarca

6 :01x06 - An Innocent Man (a.k.a You're No Jack McCallister)

Oct/17/2004
At the college, one of Grace's collegues is accused of sexual harassment. Grace defends him until new and startling evidence is uncovered. Bobby, after spending too much time with Dex, cheats on a test to bring his grades back up. Jack is surprised to find that Missy and Courtney have become friends.
Guest Stars: Freda Foh Shen as Miriam Chen-Pew | Tess Harper as Karen Carmichael | Jeanette Brox as Dex Truggman | Shonda Farr as Stacy | Don McManus (1) as Professor Steven Feltz | Evan Handler as Cary Donovan | Aaron Lustig as Committe Spokesman | Amanda Barfield as Rose | Sage Mears as Mr. Minkin | Polly Cusumano as Sara Ehret | Ed Begley, Jr. as Rev. Belknap
Director: Thomas Schlamme

7 :01x07 - Valentino

Oct/27/2004
Grace catches Dex and Bobby together, then teams up with Jack to get the two to break up. Courtney wants to date a frat boy, but Peter won't let her do so. In scenes from the future, we learn that President McCallister had problems controlling one of his sons, Jack, and the secret service.
Guest Stars: Jeremy Garrett as Dave Wild | Shailene Woodley as Chloe | Eva Simone Fisher as Ani Wannabe | Steele Justiss as The Grungy Guy | Shawn Carter Peterson as The Clerk | Cliff DeYoung as Mr. Truggman | Jeanette Brox as Dex Truggman | Mary Gordon Murphy (1) as Martha | Brenda Wehle as Future Courtney McCallister | Dakin Matthews as Merle Horstadt | Alicia Coppola as Abigail Marks | Lawrence Pressman as Jonas Parker

8 :01x08 - Election Night

Nov/03/2004
Bobby finds out that Jack was behind his break up with Dex, and sets out to get even. Bobby's attempts to get even causes a rift between the two brothers. Meanwhile, Grace and Tom smoke pot together, which ends up to be a mistake. Later, the results of the 2004 election come in and scenes from the future reveal the outcome of the 2040 presidential election.
Guest Stars: Beth Fisher as Customer | Jeanette Brox as Dex Truggman | Evan Handler as Cary Donovan | Dakin Matthews as Merle Horstadt | Scott Foley as Lars Christopher
Director: Keith Samples
Writer: Erik Oleson

9 :01x09 - Chess Lessons

Nov/10/2004
Grace attends dinner at Missy's house, despite Jack not wanting her to. As Jack predicted, Grace embarasses him after she loses her cool over the Reverend's political beliefs. Later, Grace and Tom share a romantic encounter. Meanwhile, Bobby starts spending more time with Peter by intentionally losing chess matches and flash-forwards to the future reveal how President McCallister used chess as a war strategy.
Guest Stars: Adam Hendershott as Garrett | Steven C. Nelson as College Guy | Samantha Quan as Megan | Pamela Roylance as Mrs. Evelyn Belknap | Sam Horrigan as College Guy | Adam McArthur as The Guy | Jonathan Redford as The Roomie | Ed Begley, Jr. as Rev. Belknap | Hector Elizondo as Gerald Cruz
Director: David Petrarca

10 :01x10 - Lost Boys

Nov/17/2004
Jimmy, Grace's gay brother, visits the McCallisters for Thanksgiving. At first, everyone is happy about his visit, but their feelings soon change after he gets put in jail. Meanwhile, Matt, one of Jack's teammates, develops a crush on him. Jack's reaction to the crush sends Matt into a deep depression, and ends up committing suicide. Jack becomes distraught when he feels responsible.
Guest Stars: Beau Wirick as The Teammate | Stephen Mendel as Mr. Saga | Nikki Griffin as Cheerleader #1 | Aasha Davis as Cheerleader #2 | Shawna Riggio as Cheerleader #3 | Rachel Melvin as Jamie | Jayne Brook as Mrs. Kramer | Shonda Farr as Stacy | Barbara Eve Harris as High School Teacher | Kathy Baker as Carol Bryson | James Eckhouse as Mr. Kramer | Dakin Matthews as Merle Horstadt | Ron Canada as Marcus Ride (adult) | Thomas Cavanagh as Jimmy McCallister | Patrick J. Adams as Matthew Kramer
Director: Bryan Gordon

11 :01x11 - Today I am a Man

Dec/01/2004
Grace runs into Jack at the supermarket while he's in line to buy condoms. Grace tries to be supportive and talk to him about whether or not Missy is the one he wants to be with, but Jack is reluctant to talk with her. Meanwhile, Grace has to give some tough love to Jimmy when he returns to his old ways. Bobby tries to get Warren and Deena together, but Warren is hurt when she tells him that she likes Bobby.
Guest Stars: Beverly Nero as Warren's Mom | Josh Holt as Mercer | Thom Gossom, Jr. as Mr. Ride | Saul Rubinek as Nahum Mayhew | Courtney Jines as Deena Greenberg | Thomas Cavanagh as Jimmy McCallister | Dean Collins as Warren Feide
Director: Michael Schultz

12 :01x12 - Running Scared

Jan/26/2005
Jack tries to go back to his normal life after his attack, but is having trouble adjusting to his injuries. Grace gets caught leaving Tom's apartment by one of her students, who uses what she saw to blackmail Grace into getting a high grade. Meanwhile, Courtney tries to get close to a college boy, but is let down when he doesn't have the same feelings. Lastly, scenes from the future reveal how President McCallister dealt with a devistating bombing in Chicago.
Guest Stars: Nicole Cavazos as Kappa Sister #1 | J.K. Simmons as Cyrus Miller | Shailene Woodley as Chloe | David Purdham as Dr. Battles | George Wyner as Faculty Professor #1 | Virginia Williams as Natalie Schultz | Richard Tillman as Chet | Christina Cindrich as Kappa Sister #2 | Dakin Matthews as Merle Horstadt | Mike Erwin as Nate Edmonds
Director: Perry Lang

13 :01x13 - A New Frontier

Feb/02/2005
Bobby begins to catch on to Grace and Tom's relationship after he goes on a camping trip with Grace and him. Jack and Missy's relationship struggles when Missy begins to focus her attention on Randy instead of Jack. Courtney's relationship with Nate continues to progress. Meanwhile, Jack meets Katie at his doctor's office and an unlikely friendship emerges. Future scenes show how President McCallister backs space travel to Mars.
Guest Stars: Amy Watt as Deborah Finch | Myra Turley as The Nurse | Cam Gigandet as Randy Bongard | Kate Mara as Katie | Mike Erwin as Nate Edmonds
Director: David Petrarca

14 :01x14 - Into the Woods

Feb/09/2005
Jack walks in on Tom and Grace, leading Jack to tell Grace what he thinks of the relationship. Bobby talks Grace into letting him go on a hunting trip with Peter, but the experience wasn't what Bobby had imagined it to be. Meanwhile, Courtney and Nate take their relationship to the next level, and Jack begins to hang out with Katie while he deals with Courtney and Randy's new relationship.
Guest Stars: Chad Brokaw as Jordan | Sharon Madden as College Nurse | John Heard as Dennis Morgenthal | Dean Collins as Warren Feide | Kate Mara as Katie | Cam Gigandet as Randy Bongard | Mike Erwin as Nate Edmonds
Director: Perry Lang

15 :01x15 - Time Out of Life

Feb/16/2005
Grace and Tom's relationship is exposed when a collegue catches them kissing in Grace's office. Jack and Katie continue to get closer. Bobby and Warren have a sleepover in an attempt to become popular at school. But when a severe snow storm hits Hart, Tom, Warren, Bobby, and the other boys at the sleepover are snowed in, and across town, Jack, Courtney, Missy and Katie are also trapped together. There, the foursome plays truth or dare, and Jack winds up kissing Courtney on a dare. Grace is trapped in Peter's office, and Peter asks Grace for advice about Courtney and Nate's relationship.
Guest Stars: Crawford Wilson as Scott | Jascha Washington as Brad Whistler | Quinton Medina as Keith | Kyle Gallner as BJ Bongaro | Brenda Wehle as Future Courtney McCallister | Blaine Miller as Joel | George Wyner as Faculty Professor | Dean Collins as Warren Feide | Kate Mara as Katie | Cam Gigandet as Randy Bongard | Mike Erwin as Nate Edmonds

16 :01x16 - And Justice for All

Feb/23/2005
Peter takes action against Grace and Tom's relationship, leading Grace to face the Ethics Committee. Bobby and Warren land a job cleaning out Mrs. Sorensen's garage, and they find evidence that connects Mrs. Sorensen's grandson to Jack's attack. Jack and Marcus try to take action against Jack's attacker, but each one of their plans falls through.
Guest Stars: Stephen Monroe Taylor as Tim Swain | Eric Allan Kramer as Officer Burke | Jeff Hayenga as Ethics Chairperson | Thom Gossom, Jr. as Mr. Ride | George Wyner as Roger Hennessy | Will Collyer (1) as Geza | Danica McKellar as Keirsten (Student Committee Person) | Mike Erwin as Nate Edmonds | Dakin Matthews as Merle Horstadt | Dean Collins as Warren Feide | Ron Canada as Marcus Ride (adult) | Pat Crawford Brown as Mrs. Sorensen
Director: David Petrarca
Writer: Erik Oleson

17 :01x17 - Querida Grace

Mar/02/2005
For a school assignment, Bobby has to research his family's history. Bobby's research lead to more questions than answers about his past. Jack and Katie's budding relationship continues to progress, but Courtney and Nate's ends after Jack sees Nate cheating. Grace and Tom continue to deal with the aftermath of their affair.
Guest Stars: McNally Sagal as Mrs. Betts | Will Collyer (1) as Geza | Kyle Gallner as BJ Bongaro | Luis Avalos as Mr. Luis | Blaine Miller as Joel | Neil Patrick Harris as Preston Phelps | Dean Collins as Warren Feide | Mike Erwin as Nate Edmonds | Kate Mara as Katie | Torrey DeVitto as Tiffany
Director: Arvin Brown

18 :01x18 - Friends with Benefits

Apr/13/2005
Grace has to adjust to having a new TA, now that Tom is no longer around. Grace meets up with an old collegue, but is scared that he'll find out about her affair with Tom. Jack disapproves with Bobby wanting to join the track team. Meanwhile, Jack learns that his relationship with Katie wasn't what he thought it was, and is suprised to learn that Marcus and Courtney may have feelings for each other. Lastly, Missy talks to Jack and reveals some startling news.
Guest Stars: Randy Wayne as Frank | Marissa Jaret Winokur as Margaret | John Heard as Dennis Morgenthal | Cam Gigandet as Randy Bongard | Kate Mara as Katie | Dean Collins as Warren Feide
Director: Sheldon Larry

19 :01x19 - A Child of God

Apr/20/2005
Missy's suspicions are confirmed when the school nurse tells Missy she's pregnant. Jack and Missy tell their parents and they come together to discuss what actions should be taken. However, things don't go well and Missy is thrown out of her house. Grace agrees to take Missy to have a procedure done. Meanwhile, Bobby decides he wants to be baptized, but can't until a family member agrees to accompany him.
Guest Stars: Laura Richardson as Teacher | Pamela Roylance as Mrs. Evelyn Belknap | Ed Begley, Jr. as Rev Balknap

20 :01x20 - Under the Influence

Apr/27/2005
After an argument at a school dance, Randy, Missy, Courtney, and Jack decide to go to an after-party. However, they never reach their destination due to a deadly car accident, where one of the four is killed. Meanwhile, Grace chaperones Bobby's field trip, much to his embarassment. Scenes from the future reveal that one of President McCallister's children was killed in a drunk driving accident and the situation around the accident.
Guest Stars: Justin Kirk as John "Jack" McCallsiter | Kate McGregor-Stewart as Mrs. Opal | Crawford Wilson as Scott | Blaine Miller as Joel | Gabriel Sunday as The Hopeful Guy | Dean Collins as Warren Feide | Cam Gigandet as Randy Bongard | Kate Mara as Katie
Director: Perry Lang

21 :01x21 - Stand By Me

May/04/2005
The aftermath of the accident begins to set in. Missy's parents are distraught after learning of her death, and Jack lies to the police about who was driving in order to protect Marcus. However, Marcus is racked with guilt and eventually confesses to his father, who is torn about what to do. Meanwhile, Warren learns that he's moving and Bobby has a hard time saying goodbye.
Guest Stars: Harry Groener as Adult Warren Fiede | Suzanne Ford as Mrs. Greenburg | Pamela Roylance as Mrs. Evelyn Belknap | Thom Gossom, Jr. as Mr. Ride | Dean Collins as Warren Feide | Ed Begley, Jr. as Rev Balknap
Director: David Paymer

22 :01x22 - Legacy

May/11/2005
In an episode that details the future, a voice over explains the brother's futures. Jack fights in the War of Americas and is badly injured. He later becomes a public defender, a Congressman, but his life is tragically cut short buy a drug addict. Bobby takes over Jack's seat in congress. The episode ties in the boy's visit to with their father, Juan, in prison where Jack decides to meet him. Juan explains his reason for leaving and how he was wrongly convicted. This drives Jack to be a public defender. Lastly, Jack reveals his feelings to Courtney and Tom returns to see Grace.
Guest Stars: Lou Diamond Phillips as Juan Alberto Alba | Norman Lear as Future Peter Benedict | Tim Robbins as Pres. Robert McCallister (voiceover) | Gore Vidal as Documentary Host
Director: Michael Schultz
Warning: Jack & Bobby guide may contain spoilers
Classification: Scripted
Genre: Drama
Status: Canceled/Ended
Network: WB ( USA)
Airs: Sundays at 09:00 pm
Runtime: 60 Minutes
Premiere: September 12, 2004
Ended: May 11, 2005
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