History TearJerker / TheMaskedSinger

** Goldfish makes another heartbreaking revelation during Queen Night: she lost her biggest supporter (a photo seen in her Clue Package heavily implies this person to be her father) right before taking on a big role. Goldfish can heard heard tearing up as she talks about how she found the strength to perform despite her grief and Rita is similarly left in tears after the Clue Package and performance. Later on, as she theorizes that Goldfish could be Creator/VanessaHudgens, Rita highlights how she considers Vanessa a friend who was nice to her when she first arrived in the United States and tearfully empathizes with Vanessa for the 2016 loss of her father.

* During Transformer's Night, Goldfish is revealed to have a messy love life, mentioning how not only was one of her break ups public, but ''[[NoSympathy people made [=TikToks=] about it.]]''

** When her clue reveals she has a connection with Robin, she admits that she worked with his dad and struggles to keep herself from tearing up, implying that she misses him just as much as Robin.

* Poodle Moth's Clue Package on TV Themes Night sees her talk about how her father [[ParentalAbandonment walked out of her life without warning]] and never read the letters she tried to send him, leaving her heartbroken and damaging her self-worth. It turns into a happy tearjerker, however, when Poodle Moth mentions how she grew through the pain and learned to love herself, as symbolized by her writing a letter to ''herself''.

* Poodle Moth's Clue Package on TV Themes Night sees her talk about how her father [[ParentalAbandonment walked out of her life without warning]] and never read the letters she tried to send him, leaving her heartbroken and damaging her self-worth. It turns into a happy tearjerker, however, when Poodle Moth mentions how she grew through the pain and learned to love herself, as [[Bookends symbolized]] by her writing a letter to ''herself''.

* Anteater's First Clue Package as a whole, talking about how the trappings of fame took a toll on his personal life and his sense of identity. It takes a turn for the heartwarming, though, when he goes on to describe how he [[EarnYourHappyEnding managed to rebuild his life and start a family with his true love]].
* Hawk revealing in his "Harry Potter Night" clue package how someone close to him lost her battle with cancer and how it led him to a dark place before he was able to open up and get the mental help he needed.
* Donut's Clue Package on "Trolls Night" is absolutely heartbreaking to listen to, especially when he talks about how he lost [[TheLostLenore his beloved partner]] and how difficult life has been since she passed away, calling her "My Smile". Poor Donut is audibly crying throughout this part of the package, and the whole panel is also in tears.
** The whole panel is in floods after Donut's performance, particularly Robin, who knows all too well the pain of losing a loved one. Donut's choked up response to Robin's praise is gutwrenching.
-->'''Donut:''' I thank you very much. [[InMemoriam It was all for her.]]

* The appearance of anyone who died after their time on the show, contestant or otherwise, can be considered this in hindsight. So far, these include Bob Saget[[note]]appeared in Season 4 as Squiggly Monster, died in January 2022[[/note]], Leslie Jordan[[note]]appeared as a guest panelists in Seasons 6, 7, and 8, died in October 2022[[/note]], Kirstie Alley[[note]]appeared in Season 7 as Baby Mammoth, died in December 2022[[/note]] and Jerry Springer[[note]]appeared in Season 8 as Beetle, died in April 2023[[/note]].

* The appearance of anyone who died after their time on the show, contestant or otherwise, can be considered this in hindsight. So far, these include Bob Saget[[note]]appeared in Season 4 as Squiggly Monster, died in January 2022[[/note]], Leslie Jordan [[folder]]appeared as a guest panelists in Seasons 6, 7, and 8, died in October 2022[[/note]], Kirstie Alley[[note]]appeared in Season 7 as Baby Mammoth, died in December 2022[[/note]] and Jerry Springer[[note]]appeared in Season 8 as Beetle, died in April 2023[[/note]].

* The appearance of any contestant who died after their time on the show can be considered this in hindsight. So far, these include Bob Saget[[note]]appeared in Season 4 as Squiggly Monster, died in January 2022[[/note]], Kirstie Alley[[note]]appeared in Season 7 as Baby Mammoth, died in December 2022[[/note]] and Jerry Springer[[note]]appeared in Season 8 as Beetle, died in April 2023[[/note]]. And while he didn't compete on the show, guest panelist Leslie Jordan's passing in October 2022 holds the same weight as the aforementioned contestants' deaths.

* The appearance of any contestant who died after their time on the show can be considered this in hindsight. So far, these include Bob Saget[[note]]appeared in Season 4 as Squiggly Monster, died in January 2022[[/note]], Kirstie Alley[[note]]appeared in Season 7 as Baby Mammoth, died in December 2022[[/note]] and Jerry Springer[[note]]appeared in Season 8 as Beetle, died in April 2023[[/note]]. And while he didn't compete on the show, guest panelist Leslie Jordan's passing in October 2022 holds the same weight as the aforementioned contestants.

* The appearance of any contestant who died after their time on the show can be considered this in hindsight. So far, these include Bob Saget[[note]]appeared in Season 4 as Squiggly Monster, died in January 2022[[/note]], Kirstie Alley[[note]]appeared in Season 7 as Baby Mammoth, died in December 2022[[/note]] and Jerry Springer[[note]]appeared in Season 8 as Beetle, died in April 2023[[/note]].

%%* Anteater's First Clue Package as a whole comes off as this.