On August 21, 1998, Gary Barber, former vice chairman and COO of Morgan Creek Productions, together with Roger Birnbaum, co-founder and former head of Caravan Pictures, founded Spyglass Entertainment.

The startup company signed a five-year distribution agreement with the Walt Disney Studios, which took an equity stake.

On October 29, 1998, European media conglomerates Kirch Group and Mediaset invested in theatrical, video and television distribution rights to between 15 and 25 films in Germany, Italy, Spain, Poland and the former Soviet Union for over five years.

[6] M. Night Shyamalan's The Sixth Sense (released 1999), Spyglass's second film after Instinct, grossed $661 million at the global box office.

[8][9] On March 7, 2003, Spyglass Entertainment agreed to a four-year distribution output deal with Village Roadshow for Australia, New Zealand and Greece.

[13] On December 20, 2010, Gary Barber and Roger Birnbaum became co-chairmen and CEOs of the holding company of Metro-Goldwyn-Mayer (MGM), which had at that time recently emerged from bankruptcy.

[14] On March 13, 2019, Barber and Lantern Entertainment revived the company as Spyglass Media Group, bringing in Eagle Pictures and Cineworld as investors.

[2] Damien Marin followed Barber from MGM to be appointed Spyglass president of worldwide distribution and acquisitions on September 3, 2019.