Rather than fully review the series itself as many reviewers have done, I will take a different angle and tell a little of the show's background as many have forgotten or altogether overlooked it.
Jack & Bobby was one of the handful of unwatched--but excellent--television series of the first decade of the 21st Century. The 2004-2005 season in particular generated some great new series across the board, of which this series was one. Many critics hailed the show as "too good for American television"...and they were right, it was.
Even though it didn't last beyond its first season, the show's producer's saw fit to give the show a proper beginning, middle, and end, as if they had planned to run the show for just one season all along. It had an unusual pairing of creative teams: the producers of "Everwood" and "The West Wing", both well written but vastly different television programs, but nonetheless gave this series a unique take on storytelling, which perhaps itself led to its demise. While many of its most loyal fans--I consider myself among them--thought the use of the "future documentary" wrap around segments were brilliantly used as a window into the family's future, others found them confusing. If you didn't understand the premise, these segments could possibly take you out of the story entirely, which I presume is what happened to a large amount of the viewers who tuned into the show in its first weeks and earned it a "back nine order". Critics and The WB itself rallied behind the show, though, and President of Entertainment Jordan Levin later stated that canceling the show was one of the hardest decisions he ever had to make. The fact that Levin allowed the show to have the dignity to finish its entire order without reducing its episode count like many failing series serves as proof to this dilemma.
The quality of this series is superb and there is some amazing writing and acting here. I really think the show is best viewed as a "binge watch"...newer viewers will "get" the show much easier if it is viewed 3-4 episodes at a time. You will also find that the show featured many "up and coming" stars, and also some familiar faces from co-creator Greg Berlanti's other series. Stars John Slattery, Matt Long, and Jessica Pare ALL later worked together again on the ever popular cable series "Mad Men", while Logan Lerman has saw a successful career on the big screen. By the time this series came around, Christine Lahti (wife of series co-creator/producer Thomas Schlamme) was already a star in her own right, and has found even more success afterward. Mike Erwin had been a recurring guest on Berlanti's "Everwood" over the two seasons preceding this series as was Kate Mara, and Keri Lynn Pratt went on to guest star on Berlanti's post-"Everwood" gig, "Brothers and Sisters". Speaking of "Brothers and Sisters", Berlanti also took the character of Robert McCallister and his political career over to the ABC hit, including the character details that he had a son named Jack and an ex-wife named Courtney. A reference to Warren's bar mitzvah was even made in an early B&S episode. The character did wind up having a much different fate than the Jack & Bobby character however.
Anyway, if you were ever a fan of "Everwood", "The West Wing", "Mad Men", or "Brothers and Sisters", there is no doubt you will enjoy viewing this short series. And the show doesn't end the way many shortlived programs do...there is an excellent series finale that ties up all loose ends waiting for you at the conclusion of the show's epic run. You'll also enjoy hearing John Williams' score from "The Patriot" (which co-starred Logan Lerman himself) over the credits for 20 of the show's 22 episodes.
I highly recommend this show for anyone who likes sophisticated and unique films and TV.