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"Shades of Gray" is the twenty second and final episode of the second season of the American science fiction television series Star Trek: The Next Generation, the 48th episode overall. It was originally broadcast on July 17, 1989, in broadcast syndication. It was the only clip show filmed during the series, and was created as such to meet a budget shortfall at season's end due to prior episodes that had cost overruns. Set in the 24th century, the series follows the adventures of the Starfleet crew of the Federation starship Enterprise NCC 1701 D. In this episode, Commander William Riker (Jonathan Frakes) undergoes medical treatment by Dr. Katherine Pulaski (Diana Muldaur) for an alien infection and must relive numerous past events. It was the final episode written by Maurice Hurley, who originated the idea and wrote the first draft of the script, with Hans Beimler and Richard Manning conducting re writes. It was directed by Rob Bowman and the framework sequences were filmed over the course of three days. It was watched by 9.8 million viewers on the first broadcast, the highest ratings for the series since "Samaritan Snare" two months earlier. "Shades of Gray" is widely regarded as the worst episode of the series, with critics calling it "god awful" and a "travesty"; The reason was that the show had overspent on the episodes "Elementary, Dear Data" and "Q Who", and Paramount Pictures was holding the series to their overall season budget. It was the last episode on which Maurice Hurley acted as head writer; he referred to the episode as a "piece of shit" and "terrible, just terrible". He turned in the idea of a cheap clip show to save money and wrote the first draft of the script, with Richard Manning and Hans Beimler conducting re writes. Ron Jones created the music for the episode, including a three note motif to represent the virus that infects Riker. Themes build as the episode progresses, with elements from "Infection Spreads" which is played over the scene between Riker and Troi move into the pieces "Shades of Pleasure" and "Earth Boys Are Easy" which is played over the pleasurable memories. String instruments and flutes are added to "Shades of Sadness" which played over the unhappy memories, before it built to a climax in the intense memories in the pieces "Critical Condition", "Shades of Conflict" and "Final Intensities". Several scenes retained the compositions from the episodes, including pieces by Dennis McCarthy, while others by McCarthy were re composed by Jones.

"Shades of Gray" was first shown on July 17, 1989 in broadcast syndication. It was the final episode of the second season and was watched by 9.8 million viewers on the first broadcast. It was the highest number of viewers for an episode since "Samaritan Snare" some two months prior. Several reviewers re watched the episode after the end of the series. In 2011, Keith DeCandido watched "Shades of Gray" for Tor. com, and admitted that he hadn't seen the episode since the original broadcast. He said that it was a "trainwreck" and even worse than he remembered, because other shows such as Xena: Warrior Princess and Stargate SG 1 had since done much better clip shows. Michelle Erica Green in her review for TrekNation called the storyline "absurdly flimsy" and that the episode "just felt lazy on every level". It was also the original choice of worst episode by Empire magazine, but it was decided that it didn't count because it was a clip show – so "Masks" was chosen instead. In 2016, fans at the 50th anniversary Star Trek convention voted "Shades of Gray" as the fifth worst Star Trek episode, of any series, and the second worst episode of this series, with only "Code of Honor" faring worse. In 2017, this episode was rated the 7th worst episode of the Star Trek franchise up to that time, by Screen Rant, and explained several issues with the episode including a lack of meaning in the clip segments. In 2019, they ranked it the 6th worst episode of the franchise based on IMDB rankings. Ars Technica and ABC News Australia noted that "Shades of Grey" had by far the lowest IMDb rating of any episode in the franchise. Ars Technica pointed out it had been "hobbled" by the 1988 writer's guild strike, and did not include it among what they considered to be the five worst episodes of the series.

The first home media release of "Shades of Gray" was on VHS cassette, appearing on October 12, 1994 in the United States and Canada. The episode was later included on the Star Trek: The Next Generation season two DVD box set, released in on May 7, 2002. The episode was released as part of the season two Blu ray set on December 4, 2012.