Bop It
The "fast talking, electronic" 1996 Hasbro game told players to "bop it, twist it, pull it, pass it" in its 1998 carnival-themed ad.
Nintendo Game Boy
The original Game Boy, which came out in 1989, turned 30 this year. It's led to dozens of successors; its first update in-color, Game Boy Color, was released in 1998.
Sony's robot dog, Aibo ERS-110
Sony put out its first Aibo robot dog, the ERS-110, 20 years ago in 1999. After a 12-year Aibo hiatus starting in 2006, Sony came back with Aibo ERS-1000 in 2018.
Cannon Powershot
The first of Canon's PowerShot series of point-and-shoot cameras was the model 600, released in 1996.
TiVo
The first TiVo DVR (digital video recorder) rolled out in 1999.
USB Flash Drive
The first patent for the USB flash drive was filed by M-Systems in 1999, and the first USB flash drive sold was the ThumbDrive by Trek 2000 International in 2000.
VHS
The first VHS videotape was released in Japan in 1976 and made it stateside in 1977.
CD
The CD was first released in Japan in 1982 and Europe in 1983.
Smartphone
The first smartphone was the the IBM Simon Personal Communicator, released in 1994. It featured a touchscreen and apps (e.g. calculator, calendar, mail, address book, notepad).
DVD
We've had DVDs since the mid-90s. Sony, Philips, Toshiba, and Time Warner were involved in creating the common DVD format agreed upon in 1995.
Cassette
Philips released the Compact Cassette in 1963. That means we've been dropping fire mix-tapes for over 50 years now.