Chicago

1986 · John Hughes · 103 min · Comedy

A joyful celebration of seizing the day that remains one of the most quotable and rewatchable comedies of the 1980s, powered by Matthew Broderick's irresistible charm.

2009 · 7 Seasons · CBS · Drama / Legal

The Good Wife opens on a politician's wife standing beside her husband at his scandal press conference, and spends seven seasons turning that silent woman into the most formidable character in the room. Julianna Margulies's Alicia Florrick anchors the case widely made for this as the last great network drama, a show that ran twenty-two episodes a year while out-writing most of cable, with a supporting bench, Josh Charles's Will, Christine Baranski's Diane, Archie Panjabi's Kalinda, and a rotating repertory of judges and rivals, that remains the envy of the form. A shocking mid-series rupture produced its finest hour. The last two seasons and a slap-based finale spend down some goodwill. The peak years remain untouchable.

2022 · 4 Seasons · FX (on Hulu) · Comedy-Drama

The Bear built its reputation on two seasons of extraordinary television, driven by performances and filmmaking that set a new standard for how stories about work, grief, and family could be told on screen. Jeremy Allen White anchors a cast that brings real emotional weight to every frame, and the show's portrayal of kitchen culture feels lived-in and honest. Season 3's stumble into pacing issues and narrative drift is a real blemish, not an imagined one, though Season 4 clawed back meaningful ground. Taken as a whole, this is a show that reaches genuine greatness more often than it falls short, and its best stretches rank among the finest hours of modern television.

2003 · Erik Larson · 447 pages · Nonfiction

Erik Larson's dual narrative about the 1893 Chicago World's Fair and serial killer H.H. Holmes is one of the most popular works of narrative nonfiction published this century. The fair sections are richly detailed and often fascinating, and Holmes provides a genuine sense of menace. The book's weakness is that the two stories never fully merge, leaving readers with two good books interleaved rather than one great one. Still, for readers who enjoy history written with the pace and tension of a thriller, this delivers.

2019 · 2-4 Players · ~120-180 min · Competitive

City of the Big Shoulders captures the ruthless energy of 1871 Chicago's economic boom through a stock-holding game that rewards shrewd investment and timing, offering one of the most accessible entries into the 18XX-adjacent economic genre.

2011 · 11 Seasons · Showtime · Comedy-Drama

Shameless built one of television's most unforgettable families, combining raw comedy with genuine heart in its early seasons before an eleven-year run inevitably diluted what made the Gallaghers special.