Most Amusing Celebs Paparazzi Encounters From 90s

Whether you believe it or not, there was a time when social media did not exist, and celebrities weren’t exactly only a click or a follow away. The only chance for fans to get a glimpse of our favorite stars was to rely on paparazzi photos or in rare cases spotting them somewhere in the streets.

Before the tech-savvy 2000s, ’90s era celebs were the rulers of the streets of Hollywood. In this post, we’ve listed 15+ photos of celebrities’ most amusing paparazzi encounters. From young Leonardo DiCaprio to hilarious shot of Will Smith – this list is featuring some of your most favorite superstars. Scroll on peeps. Don’t forget to comment on your favorite ones!

#1 Ryan Phillippe and Reese Witherspoon captured in Los Angeles in 1999.

#2 Brad Pitt and Jennifer Aniston in similar cargo pants out shopping in L.A. in 1999.

#3 Johnny Depp and Kate Moss walk hand-in-hand clad in matching leather jackets in 1994.

#4 Tom Cruise and Nicole Kidman caught by the paps in matching white blouses, circa 1995.

#5 Princess Diana leaving a London country club in a Virgin Atlantic Sweatshirt, 1995.

#6 Mariah Carey in a head-to-toe velvet ensemble in 1990.

#7 Will Smith departs on a press tour, 1991.

#8 Brooke Shields and Michael Jackson attend the 35th Annual Grammy Awards together, 1993.

#9 Winona Ryder leaving a film premiere in leather and denim, 1991.

#10 Robert Downey Jr. and Sarah Jessica Parker dine together in 1990.

#11 Young Leonardo Dicaprio on the streets of Hollywood, 1995.

#12 Kate Moss and Naomi Campbell exit a London Fashion Week party in 1993.

#13 Cindy Crawford is caught by the paparazzi in 1991 at the Los Angeles Airport.

#14 John F. Kennedy Jr. and Carolyn Bessette at a Whitney Museum Fundraiser, 1999.

#15 Bobby Brown, Whitney Houston, and Bobby Christina arrive at LAX, 1995.

#16 Ben Affleck and Gwyneth Paltrow arrive at the Los Angeles International Airport, 1999.

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