© 2026 ABC News

When Peter is mistakenly sent a check for more $150,000, he dumps the cash from a blimp at the Super Bowl and gets arrested before his family finds a way to bail him out.

It pays off to follow the most-watched television event every year. The \"Family Guy\" pilot garnered 22 million viewers that night.

Pop Culture: A Pop Princess Ruled the Airwaves

After Britney Spears' first album, \"... Baby One More Time,\" debuted in the fall of 1998, and the single by the same name climbed its way to the top of the Billboard Top 100 chart in the new year and stayed there for two consecutive weeks. Both the album and single were No. 1 when Super Bowl 33 aired.

\"PHOTO:
Amazon
PHOTO: When Super Bowl XXXIII aired on Jan. 31, 1999, Britney Spears? inaugural album "Baby One More Time" was at the top of the Billboard charts.
>

The highest-ranking television show for the 1998-99 season was \"ER,\" followed by \"Friends\" and \"Frasier.\"

No. 1 at the box office was quintessential teen romance movie \"She's All That,\" starring Freddie Prinze Jr. and Rachael Leigh Cook.

Instead of watching the game, kids were playing with their Nintendo Game Boy Color and Furbies, both of which were among the most-sought-after toys for Christmas the month before.

\"PHOTO:
Andy Cross/The Denver Post via Getty Images
PHOTO: Furby was one of the year's hottest toys.
>
\"The
Philipp Zechner/Alamy
The Nintendo Gameboy Color, released the year before, was all the rage at the beginning of 1999.
>

What's old is sometimes new again. By the end of the 1990s, the extreme trends -- bright-colored prints, overalls and jelly sandals -- began to die down. What was left were the staples, such as lingerie-inspired slip dresses, choker necklaces and denim dresses, which have circulated back in style.

\"PHOTO:
Steve Eichner/Getty Images
PHOTO: Gwyneth Paltrow wearing a choker in New York, Dec. 8, 1999.
>
\"PHOTO:
Dave Benett/Getty Images
PHOTO: Models Naomi Campbell and Kate Moss attend the De Beers/Versace 'Diamonds are Forever' celebration at Syon House on June 9, 1999 in London.
>

Advancing Technology and Smartphones Had Not Yet Changed Lives

People who attended Super Bowl 33 actually watched the game because smartphones and the plethora of apps they offer were not yet around.

So instead of being distracted by taking selfies and checking how many “likes” they got on Facebook, Twitter, Instagram and Snapchat, people were probably devoting a much larger percentage of their focus to the gridiron.

Most Americans didn't even have cellphones, yet. There were only about 86 million cellphone subscribers in the United States in 1999, compared to more than 300 million today.

After its release in 1998, the Nokia 6210 was among the best-selling cellphones. It was loaded with everyone's favorite -- and only -- game: Snake.

\"Apple
Clynt Garnham Technology/Alamy
Apple wouldn't debut the iPod until 2001, so portable CD players were still being used for on-the-go music.
>

Apple wouldn't release the iPod until 2001, so music lovers were forced to carry around portable CD players for on-the-go listening. The days of lugging around heavy zip-up books full of CDs are not missed.

ABC News' Celina Fang contributed to this report.

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