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May is the fifth month of the year and contains 31 days. There are 7 months remaining until the end of the year.
- On May 1, 2018, Mari Takahashi and Joshua Ovenshire become freelancers and are no longer employees of Defy Media, but will continue to appear in Smosh Games videos.
- On May 22, 2020: Jacklyn Uweh was officially inducted into the Smosh Family.
- On May 4, 2021: Smosh Producer and Director Sarah Whittle officially announced her departure from Smosh.
- May 18, 1987: Smosh Family member, Joshua Ovenshire, better known as Jovenshire, was born.
- May 23, 1988: Smosh Family member Wesley Johnson, better known as Wes, was born.
- May 31, 1987: former Smosh Family member Amra Ricketts, better known as Flitz, was born.
- May 10, 1997: Smosh guest star Brittany Broski, who starred in Smosh's first video featuring and advertising their coffee brand, was born.
- May 9, 2008: The final episode of the Ian H series A Day in the life of Smosh aired.
- May 19, 2013: SGA Spotlight began airing on Smosh Games.
- May 27, 2014: The final episode of the Smosh Games series Backseat Gaming aired.
- May 12, 2015: The Smosh sketch series Every Blank Ever began airing.
- May 30, 2016: The final episode of the Smosh series Part Timers aired.
- May 15, 2017: The final episode of the Smosh Pit series Lunchtime with Smosh aired.
- May 27, 2017: The final episode of the Smosh Pit series Smosh's Seriously Super Stupid Sleepover aired.
- May 27, 2017: What're Those!? began airing on Smosh Games, having previously aired on Smosh Games Alliance.
- May 29, 2017: The final episode of the Smosh Pit series Smosh is Bored aired.
- May 9, 2018: First Time Story Time began airing on Smosh Pit.
- May 22, 2018: 2 Truths 1 Lie began airing on Smosh Pit.
- May 7, 2019: The Smosh Pit series Eat It or Yeet It began airing.
- May 19, 2020: The Smosh Pit series Beopardy began airing.
- May 4, 2021: The SmoshCast began airing special episodes.
- May 3, 2008: Smosh's most popular video, Beef 'n Go, was released.