* "Samson" is ''haunting''.
* She also wrote the {{Tear Jerker}}s "Carbon Monoxide" and "the Flowers", but the worst is "Chemo Limo" (on ''Music/SovietKitsch''), which is about a mother of four dying of cancer. It can be tough to keep it together when she says the last line, "Oh God Barbara, she looks just like my mom"; in a tone of horrified realization. And then you realize that a lot of cancers are genetic.
** Then there is "Buildings", which chronicles a city woman's growing despair and her husband's trying to help her cope with it. It is heavily implied at that she ends up committing suicide. Regina's voice, often quirky or cheeky, has never been so soul-wrenching.
* As well, Regina's song "The Call", that plays during the end of the film version of ''Literature/PrinceCaspian'', can bring to tears anyone who has ever had to leave their friends or other loved ones behind.
* "Us" from ''Music/SovietKitsch'', which may be her most beautifully orchestrated tune.
* "Laughing With", in which Regina recites a long string of horrible, half-implied tragedies and matter-of-factly states that "nobody laughs at God" during these times. And she goes on to denounce people who treat God like a wish-granting genie used to justify their own hatred, which can inspire the good kind of tears.
** The "when it's gotten real late and their kid's not back from the party yet" line can be especially triggering.
** It can be tough for one to make it past "No one laughs at God on the day they realise that the last sight they'll ever see is a pair of hateful eyes" without letting out a sob.
** Then there is, "...when they see the one they love, hand in hand with someone else and they hope that they're mistaken." Many can probably relate to that.
** "No one's laughin' at God... when they're sayin' their goodbyes."
* "Aquarius". In one of the few live recordings of "Aquarius," she has to pause because she started crying.
* One rooted in a real life tragedy, her 2010 performance at Montreux was a dark, sad affair, coming just after the death of her cellist, Daniel Cho. She, along with many members of the audience, were in tears during the uncharacteristically somber act.
* Braille, a first-person story of a poor, lonely (and seemingly young) single mother, can really bring one to tears.
** "Braille" is positively ''brutal.''
-->''She was lying on the floor and counting stretch marks,''\\
''She hadn't been a virgin and he hadn't been a god.''
** And then you get the self-loathing...
-->''I'm still an asshole playing with candles,''\\
''Blowing out wishes, blowing out dreams...''
* "Oedipus." The chorus sounds like someone talking about their [[AbusiveParents abusive]] [[ParentalNeglect mother]], who manages to be sympathetic because she was forced to have ''[[MassiveNumberedSiblings 32]]'' kids by his father and the only way she can deal with her resentment/pain is to take it out on them or stay in her room all the time.
* "Hero". ''Especially'' if you've seen ''Film/FiveHundredDaysOfSummer''.
** Especially tear-inducing towards the end of the song, when she repeatedly mutters "its all right..." over and over, to convince herself that she doesn't "need to be saved."
* [[http://www.youtube.com/watch?v=-kTCE5Sc7F8 Her version of 'My Man']] manages to be both TearJerker and NightmareFuel due to the lyrics.
* [[http://www.youtube.com/watch?v=2oa_q6Jnukg Her version of Hallelujah]] is, yet, another one. Originally performed by TearJerker/LeonardCohen.
* "Loveology" [[http://www.youtube.com/watch?v=Qxg3DvApg34 is another one]]. Never has "forgive-me-ology" sounded so heart-wrenching.
* "The Sword and the Pen" starts out nondescriptly dark, with lines such as "The things that scare us today, what if they happen someday?" This is bad enough, but it quickly gets worse when Regina's voice gets very soft as if on the verge of tears "So what if nothing is safe? So what if no one is saved? No matter how sweet? No matter how brave?"
* "One More Time With Feeling" is both a TearJerker and a CrowningMomentOfHeartwarming at the same time. It can be interpreted as the song of a bedridden hospital patient, struggling to find the will to live in their bleak environment. Its mix of cynicism and hope combined with the warm, wavering vocals is enough to turn anyone to mush. Especially sad if you interpret the title to mean a second chance at life after a suicide attempt.
** 'Your stitches are all out, but your scars are healing wrong''\\
''And the helium balloon inside your room has come undone''\\
''And it's pushing up at the ceiling and the flickering lights it cannot get beyond...''\\
'' '''Hold on''' - one more time with feeling.''\\
''Try it again. Breathin's just a rhythm.''\\
''Say it in your mind until - you know that the words are right''\\
''This is - Why we - '''fight'''. ''\\

* "Firewood" somehow manages to give [[WesternAnimation/ToyStory2 "When She Loved Me"]] a run for its money:
--> ''Someday you'll wake up and feel a great pain ''
--> ''And you'll miss every toy you ever owned''\\
''You'll want to go back''\\
''You'll wish you were small''\\
''Nothing can slow the crying''\\
''You'll take the clock off of your wall''\\
''And you'll wish it was lying''\\

* [[http://www.youtube.com/watch?v=sXKDL6WD9CQ Her version of No Surprises]] While some have said that it lacks the warmth of the original version by Radiohead, there's something ethereal and haunting about it, and the quiet breathing near the end is absolutely unforgettable,just quiet, tired breathing of someone who has had enough of their life. As one comment by Youtube user dick sledge aptly says: I see it as a tired mother, getting home from her job middle of the night to soothe her crying child, quietly singing this lullaby to soothe the child to sleep. Promising the child that on day they will finally live a stable life with no surprises.

* "Fidelity" is a sweet love song. No tearjerking there. And then it's used in a [[http://www.youtube.com/watch?v=b-awVQkTeVE Courage Campaign video]] of gay couples begging the Supreme Court not to divorce them. Guaranteed to put a lump in your throat.
* "Small Town Moon" to anyone who wishes to leave (or has left) their hometown.
* "Two Birds", especially for fans of ''WesternAnimation/GravityFalls'' because it fits well with Dipper and Mabel [[spoiler:and Stan and Ford]].