Early 2000's TV Shows
Major League Baseball
Music
All About Chicago
Going Out On Top
100

This show debuted in 2005 and just aired it’s 16th season premiere, making it the longest running live-action American sitcom.

IT’S ALWAYS SUNNY IN PHILDELPHIA

100

Fred McGriff led the NL in Home Runs in 1992 for the San Diego Padres, the only time a Padre led the league in HRs until this man did it in 2021.

FERNANDO TATIS, JR.

100

Madonna and Britney Spears shared a kiss at the 2003 VMAs while covering what iconic 1980’s Madonna hit?

LIKE A VIRGIN

100

While Chicago is the 3rd largest city by 2022 population estimate, it is only 1/3 of the size in area of this southern city, the 4th most populated in the U.S.

HOUSTON

100

After losing the first three times he went to the Super Bowl, John Elway finished his career with back to back Super Bowl wins in the mid 90s.  Name one of the two teams he beat in his final two seasons?

GREEN BAY PACKERS or ATLANTA FALCONS

200

Punk’d aired from 2003-2007 on MTV with Ashton Kutcher pranking his celebrity friends.  After a five-year hiatus, the show returned in March of 2012 with a slew of celebrity hosts, starting with this teenage megastar musician.

JUSTIN BIEBER

200

This current player is the most recent #1 overall pick to win an MVP award.

BRYCE HARPER

200

Which artist is Calvin Broadus more commonly known as?

SNOOP DOGG

200

One of the most famous movies set in Chicago was Ferris Bueller's Day Off.  Name one of the two songs that Ferris performs during the Von Steuben Day Parade?

"DANKE SCHOEN" or "TWIST AND SHOUT"

200

This legendary New York Yankee hitter won 9 World Series championships with the Bronx Bombers, including the final three years of his career, 1949 to 1951.

JOE DIMAGGIO

300

American Idol kicked off in 2002 to much fan fare. What were the names of the 3 original judges of the show?

SIMON COWELL, PAULA ABDUL, RANDY JACKSON

300

The longest MLB win streak of all time was the New York Giants in 1916 with a 26 game heater.  Which AL team threatened this record in 2017 with a 22 game run of their own?

CLEVELAND INDIANS

300

Justin Timberlake, Britney Spears, Ryan Gosling and Christina Aguilera were introduced in the final two seasons of what 1990’s TV show revival on the Disney Channel?

THE MICKEY MOUSE CLUB

300

In 1943, Ike Sewell invented deep dish pizza at this still running restaurant.

PIZZERIA UNO

300

After a 9th Round knockout of Archie Moore in 1955, this legendary boxer retired with a record of 49-0 and as World Heavyweight Champion.

ROCKY MARCIANO

400

Despite many cancellations and inconsistent timeslots, Family Guy has seen over 20 years of success on FOX, debuting in 1999 after Super Bowl XXXIII.  Who is the only male member of the Griffin family that creator and show runner Seth MacFarlane does not voice?

CHRIS (OLDEST SON)

400

From 1998-2002, Mark McGwire, Sammy Sosa or Barry Bonds led the league or was the runner up for HRs in the NL.  Which Philadelphia Phillie slugger ended this run in 2003, leading the NL with 47 Home Runs in his first year with the team?

JIM THOME

400

What music artist released three albums between 2015-2022, ALL for which he won the Grammy Award for Best Rap Album?

KENDRICK LAMAR

400

In 1960, the first televised US presidential candidates' debate was broadcast from Chicago's CBS Studios.  Name either of the two men that were the presidential candidates.

JFK or RICHARD NIXON

400

After 19 years with the Boston Bruins, Ray Bourque was traded to this Western Conference NHL franchise in 2000, winning the Cup the following year, his final in the league.

COLORADO AVALANCHE

500

James Franco, Seth Rogan and Jason Segal co-starred on this 2000 Judd Apatow show, which lasted only 18 episodes and one season, despite positive critical reviews.

FREAKS & GEEKS

500

The 2014 Detroit Tigers starting rotation featured Max Scherzer, Justin Verlander, Rick Porcello and David Price. How many combined Cy Young awards have those four men won in their careers to date?

EIGHT

500

Every year, the MTV hosts the Video Music Awards, where they issue awards of an astronaut holding an MTV flag.  What is the more common name these trophies are known as?

MOONMAN

500

The Bean in Chicago is one of the city's biggest tourist attractions, but what is the actual name of this Millenium Park sculpture?

CLOUD GATE

500

This American swimmer won 7 gold medals at the 1972 Olympics, a record that would stand for 36 years before Michael Phelps won 8 at the Beijing Games in 2008.

MARK SPITZ