Worn by: Tom Cruise as Jerry Maguire
Reference: TAG Heuer S/el
Brand: TAG Heuer
Sports agent Jerry Maguire wears a TAG Heuer S/el Quartz Chronograph—an analog/digital watch that screams 1990s. The busy design features a three-register chronograph layout, 4:30 date window, colorful brand logo, L-shaped end links on a black leather strap, and lugs that swoop like a circus performer's mustache. The watch is visible throughout the film including during a pivotal moment when Maguire's entire career spectacularly unravels in a single day, just before his phone call to Rod Tidwell that produces the iconic "Show me the money!" line. There's no watch brand that embodies the '90s more than TAG Heuer, and Jerry Maguire nails the decade's fashion, music, and watches.
Source: https://www.hodinkee.com/articles/tom-cruise-wears-a-wacky-tag-heuer-in-jerry-maguire
Worn by: Cuba Gooding Jr. as Rod Tidwell
Reference: TAG Heuer Aquaracer
Brand: TAG Heuer
Pro football player Rod Tidwell wears a decidedly tamer two-tone TAG Heuer Professional 200m throughout the film. The watch gets its only real closeup during the final act's double-date scene at a seafood restaurant, where Tidwell's two-tone Professional fills the frame just as his wife bludgeons a crab shell with a hammer. The scene illustrates the contrast between Tidwell's grounded character and Maguire's struggle with unconditional love.
Source: https://www.hodinkee.com/articles/tom-cruise-wears-a-wacky-tag-heuer-in-jerry-maguire