Top 20 Saddest Shameless Moments
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Top 20 Saddest Shameless Moments

VOICE OVER: Kirsten Ria Squibb
"Shameless" was never sad-less. For this list, we'll be looking at the most heartbreaking moments surrounding the Gallagher family over the show's 11 seasons. Our countdown includes Fiona leaves, Carl ties to heal Frank, Monica dies, and more!

Top 20 Saddest Shameless Moments

Welcome to MsMojo, and today we’re counting down our picks for the Top 20 Saddest Shameless Moments.

For this list, we’ll be looking at the most heartbreaking moments surrounding the Gallagher family over the show's 11 seasons. Because some of these moments will reveal significant plot points, a spoiler alert is in effect.

Let us know which of these moments hit you the hardest in the comments below.

#20: Bianca Dies
“Love Songs (In the Key of Gallagher)”

Frank Gallagher has always lived his life in a - how should we put this? - carefree way. So, when he meets Dr. Bianca who only has months to live, the unlikely duo hits it off. Bianca tells Frank that she wants to get a little wild before her time is done, so she enlists the Gallagher patriarch to help her complete her bucket list. Instead of waiting out her illness, she decides to go out on her own terms by walking out into the ocean during a trip with Frank to Costa Rica. We can’t help but feel terrible for a confused and grieving Frank when he wakes up the next morning to find that she’s gone.

#19: Fiona Leaves

Fiona Gallagher had her fair share of ups and downs throughout the series, but we saw her at one of her lowest points at the end of season nine. After discovering her boyfriend is married with a child and falling on some hard times financially, Fiona spirals into heavy drinking. She decides it’s time for her to leave the South Side for good but, before she does, Frank finally acknowledges what an important role she played in the family’s life. There was not a dry eye in the house as we watched her board a plane for the first time, and when Ian sees it… Anyone else blended by their tears?

#18: Mickey Learns Ian is Joining the Army
“Survival of the Fittest”

Ian and Mickey, more fondly known through the ship name of “Gallavich,” have won over fans' hearts for more than a decade. Still, the couple had their fair share of tough moments. One of the worst came during the season three finale. Pretending to be Lip, Ian enlists, signing up for a minimum of four years away. This news obviously leaves Mickey heartbroken, and he begs for Ian to stay. It’s one of the first times that Mickey really outwardly demonstrates how much he loves him and, seeing these two so emotional about parting ways was incredibly difficult to watch. Luckily, this separation was only temporary.

#17: Fiona & Frank Fight Over Monica’s Legacy
“Requiem For a Slut”

Frank and Fiona have never seen eye to eye on much, and especially not on the subject of Monica. Following the Gallagher matriarch’s death, their raw emotions come out in an epic clash of conflicting feelings. For Frank, Monica was his great love and ultimate partner in crime. For Fiona she simply represents the loss of her own innocence, and the stone that has weighed down her entire life. As awful as Frank is, it’s still hard to see him so clearly broken over Monica’s passing. But on the other hand, it’s impossible not to feel for Fiona, whose complicated feelings about her mother are inextricably linked to decades of pain and anger.

#16: “Good Job, Fiona:

Arguably one of the best episodes of this iconic show is the series’ first, as we get introduced to this chaotic but loveable family. Frank kicks off the episode by introducing his offspring, and by the end of the episode, we see Frank and Fiona fall into their habitual roles. Frank is drunkenly passed out on the ground, while Fiona goes through a whole spectrum of emotions as she deals with him and the burden of taking on his job as a parent to her siblings. The way she completely loses it before swallowing it all back feels so real and raw. She gives herself praise on his behalf and, tragically, this is an exchange we wouldn’t get to see for real until nearly a decade later.

#15: Frank Tells Fiona about Sean
“Familia Supra Gallegorious Omnia!”

Over the course of the show, we’ve seen Fiona struggle with romantic relationships, so we were thrilled when she and Sean decided to get hitched. If anyone deserved a happily ever after, it was her. While Sean was a bit rough around the edges, he was a great match for Fiona, which is what made the subsequent events so disheartening. Sean struggled with drug addiction in the past, and right before their wedding, Frank reveals that Sean relapsed. Not only is Fiona heartbroken by this, but Sean’s son, Will, is also visibly devastated. The two ultimately break up, only adding to an ever-growing list of sorrow.

#14: Ian’s Depressive Episodes

“Shameless” did a good job of showing many different struggles faced by people every day, and Ian’s battle with mental illness was no exception. After Lip and Debbie see their brother working at a bar, they find his behavior to be totally out of the ordinary. In the episodes that follow, we see Mickey try to help Ian as he goes from being recklessly excitable to depressed and bedridden. Fiona tells a distressed Mickey that Ian may need help, as she suspects that he may have bipolar disorder. It’s certainly something that takes a toll on Ian’s loved ones, perhaps Mickey most of all.

#13: Ian Tries to Get Mickey to Talk
“Frank the Plumber”

As you may have noticed by this point in the list, a lot of the saddest moments in this show involve Gallavich - they’re put through so much… In the episode “Frank the Plumber,” Ian confronts Mickey about his sham marriage. What makes this scene so devastating is that they’re both struggling with the marriage in different ways. Mickey is clearly torn because his homophobic father forced him into this lifestyle. Meanwhile, Ian is crestfallen that he’s lost the person he cares about most and, more than that, he has to watch him live a life that he doesn’t want.

#12: Carl Finds Out What Nick Has Done

After Carl is released from juvie, fellow inmate Nick tags along. He tells Carl that he was only really happy when riding his bike as a child since it was an escape from his abusive home and addict father. Knowing this, it isn’t much of a surprise when Nick buys an identical bike to the one from his youth. What does come as a surprise is that the bike goes missing. While Nick still manages to find it again, the consequences for the young boy who ended up in possession of the bike are… horrifying. A bloodied hammer and chilling screams are all the details we need.

#11: Fiona Confronts Monica
“A Great Cause”

When Monica reappears into her kids' lives in season two, Fiona is fooled into believing that her mother has become a better person. This leads her to be a little too trusting, and Monica takes advantage of this by stealing a pool of money the kids had been saving up. A tearful Fiona would later berate her mother - to no avail, of course. While this wasn’t Fiona and Monica’s first or most infamous confrontation, it definitely still left its mark thanks to Emmy Rossum’s outstanding performance.

#10: Ian Confronts Mickey at His Wedding
“Order Room Service”

As we’ve discussed, Ian and Mickey pursued a relationship in secret, but they were discovered by Mickey’s father, and Mickey was forced to marry Svetlana. But Ian wasn’t going to give up on him without a fight. The journey to Mickey’s acceptance of his feelings for the young Gallagher was a long one, with Ian having to confront him more than once. But this scene, right before he gets married, is highlighted supremely by Cameron Monaghan, as Ian begs Mickey not to go through with it.

#9: Carl Tries to Heal Frank
“Survival of the Fittest”

By the time we caught up with the Gallagher family at the start of the show, most members of the clan had already learned the hard way how terrible their father was. But for the younger ones, it took a bit more time. In one of his more despicable schemes, Frank told Carl he had cancer in order to scam a charity foundation. He even shaved his son’s head. But when Frank ended up in the hospital from alcohol abuse, Carl did the shaving as a way to help cure his father. Carl may not exactly be the sweetest of the Gallagher kids, but seeing him do what little he could to help his dying father showed a much softer side to him.

#8: Ian and Mickey Break Up
“Love Songs (In the Key of Gallagher)”

Considering this couple had been through so much together, we couldn’t help but assume that they could withstand anything. Sadly, that wasn’t the case here. After disappearing for some time with his mother, Ian returned to break things off with Mickey. He believed that his bipolar condition was too much for Mickey to handle, and thought it best to end things then and there. The heartbreak on actor Noel Fisher’s face is so real. That being said, the sadness may have been slightly undermined by Sammy’s interruption. At least we know that this wasn’t really the end.

#7: Frank Thinks Emily Is Fiona

It isn’t too often that audiences feel bad for the Gallagher patriarch, given how despicable his behavior normally is. But this episode showed a different aspect of the character. During a hospital stint where he acquired a new liver, Frank’s medication made him mistake the young Emily for his daughter Fiona. It’s a touching moment, as this connection isn’t something we normally see with his actual daughter. Given that Emily’s father had recently abandoned her, it made the whole thing all the more tragic. The real gut punch though? When the sweet little Emily doesn’t make it and Frank thinks he’s watching his actual daughter pass.

#6: Ian Says Goodbye to His Family
“Face It, You’re Gorgeous”

Ian Gallagher has always been one of the more complex and beloved characters on the show. So saying goodbye to him, as well as Cameron Monaghan, was always going to be tough. After an act of vandalism resulted in a van exploding in Season 8, Ian pleaded not guilty due to insanity; regardless he would still end up having to serve some jail time. The blow may have been somewhat softened by Monaghan’s announcement that he was leaving the show, but watching a character we had all grown up with over 9 years say goodbye to his family was absolutely crushing. The exchange between Ian and Lip hit us hardest.

#5: Frank Calls DFS
“Cascading Failures”

Frank has let each one of his children down in various ways, but never quite like his betrayal of Fiona in this season 3 episode. Wanting revenge on his children for not letting him back into the house, Frank calls Child Protective Services on Fiona, his eldest daughter who has worked so hard to care for the family. This causes her to have to jump through multiple hoops in order to get them back. The moment when she listens to the recorded phone call and hears her father’s voice is absolutely heartbreaking. Selfish might be Frank’s default, but no one, Fiona included, could have imagined him stooping so low.

#4: Monica Dies
“Happily Ever After”

“Shameless” has mastered the art of making the audience feel conflicted about its dishonorable characters, and Monica Gallagher made us all question our feelings more than once. In the final episode of Season 7, the family was forced to say goodbye to her after she suffered a cerebral hemorrhage and wouldn’t wake up at the hospital. She was far from perfect, but the loss of her was felt by every family member. Fiona’s conversation with her troubled father afterwards put words to what we were all feeling, but there’s no single moment of grief stemming from this incident that can compare to Frank’s reaction to Monica’s stillness.

#3: Liam Almost Dies
“There’s The Rub”

When it rains, it pours. After making one terrible decision after another about her boyfriend and boss’s brother, Fiona’s secrets are found out. And having her new job and relationship tarnished because of it makes her want to blow off steam. Sadly, the result of the party she throws leaves her wishing she hadn’t indulged; Liam, the youngest member of the family at 3, gets into a stash of cocaine. Seeing his motionless body and the looks of shock on each character’s face is enough to take any viewer’s breath away. He’s never been the most crucial character to the show but seeing a child in such a state sent every viewer into a panic.

#2: Monica’s Attempt
“Just Like the Pilgrims Intended”

Before her passing, Monica traumatized the entire family at Thanksgiving. The show would go on to address the topic of mental illness with Ian in a respectable and more appropriate way, but this moment served to showcase one of the darkest events that could come from it. After going off her meds, Monica attempted to take her own life. The previous image, of family and friends gathered happily around Thanksgiving dinner, was almost serene; and it’s this juxtaposition that makes it all the more sad. The sheer terror that comes from this moment, as well as Fiona’s mournful state as she wipes up her mother’s blood afterwards, was chilling.

Before we unveil our top pick, here are a few honorable mentions.

Lip Tries to Adopt Xan, “Do Right, Vote White!”
Lip Offers Xan’s Mother Money to Adopt Her, But Has a Change of Heart

Kevin & Veronica Separate, “Tell Me You Fucking Need Me”
V & Kev Briefly Split Because He Cares More About the Kids Than Her

Lip Visits Youens in Prison, “Occupy Fiona”
After He Gets a DUI, Lip Visits His Professor & They Discuss Alcoholism

Fiona Saying Goodbye to Jimmy on His Voicemail
“Survival of the Fittest”
It’s a Soft, Sad Message

#1: Fiona’s Speech to Monica
“Nana Gallagher Had an Affair”

Fiona would spend the majority of the show unraveling the destructive actions of her mother, and her confrontation in this moment is one of the most crucial. After Monica comes back into their lives to take Liam away and begin anew, Fiona lets all of her pent-up feelings about her mother out. There would be several moments later in the series of aggression and disappointment surrounding Monica, like when she stole the family’s squirrel fund, but this scene made us appreciate just how much weight Fiona had to carry. Of course, a scene, no matter how well written, is only as good as the performer, and Emmy Rossum sure delivers.