Content warning: The following article contains discussions of depression, racism, addiction, and suicide.

Tony Soprano is one of the most acclaimed characters in television history — but also one of the most difficult. Tribute must go to the later actor James Gandolfini and Sopranos writer/creator David Chase, as both crafted a multi-faceted and wonderfully complex character that fans loved to hate.

Despite being the protagonist — and quite a charming protagonist at times — Tony Soprano was not a good person. Both in actions and personality, Tony proved to be quite a terrible human, and many viewers ended up rooting against him by the series’ end. But there’s no denying that he could also be entertaining, charismatic, and even funny.

10 Love: “Lately I’m Getting The Feeling That I Came In At The End. The Best Is Over.”

The Sopranos does a wonderful job of humanizing its deplorable lead characters. In the pilot episode, Tony sits down with Dr. Melfi and explains his feelings of missing out on the “good times,” telling her, “Lately I’m getting the feeling that I came in at the end. The best is over.” It’s a grounded sentiment, and it’s one that many viewers could easily relate to.

It provided a connection between viewers and Tony Soprano, and fans instantly fell in love.

9 Hate: “I Wipe My A** With Your Feelings!”

Tony Soprano is not a very compassionate person. Despite being depressed himself and going to therapy to treat his mental health, Tony has absolutely no sympathy for Christopher Moltisanti. Christopher feels down throughout the majority of “The Legend of Tennessee Moltisanti,” and he tells Tony that he hasn’t been feeling good.

Rather than showing some compassion and relating to Christopher, Tony instead yells at him, screaming, “I wipe my a** with your feelings!”

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8 Love: “My Father Was In It. My Uncle Was In It. Maybe I Was Too Lazy To Think For Myself.”

It’s rare for Tony Soprano to look inward and actually admit his personal problems. This is one of those rare exceptions. He explains to Melfi that the Soprano family has long had ties to the mafia, saying, “My father was in it. My uncle was in it.”

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Tony then admits that, rather than breaking away from family tradition and doing something noble, he simply decided to follow in their footsteps: “Maybe I was too lazy to think for myself.” It’s another moment that helped viewers sympathize with Tony, as they respected his self-awareness.

7 Hate: “What’s Your Background, Noel?”

Tony did a lot of horrible things throughout The Sopranos, and his despicable conversation with Noah was certainly one of his worst. Noah tries bonding with Tony through his love of film, but Tony shuns Noah for being mixed race.

Tony bluntly asks Noah, “What’s your background, Noel?” (getting his name wrong in the process, no less), and viewers know exactly what’s coming. He further tells Noah to stay away from Meadow, as he doesn’t want his daughter dating a Black man.

6 Love: “They Say Every Day’s A Gift. But Why Does It Have To Be A Pair Of Socks?”

This is by far one of the most popular quotes from The Sopranos, owing mainly to its creativity and relatable nature. Tony Soprano isn’t a very happy person, and this is his creative way of calling life mediocre, boring, and rather bland.

It once again made Tony a sympathetic and relatable character, as many viewers can’t help but feel the same way.

5 Hate: “Why Don’t You Have A F***ing Drink, Will You? Because You’re Driving Everybody Crazy With This S***!”

Christopher Moltisanti often receives the brunt of Tony’s wrath. After a period of heavy drug abuse, Christopher enters rehab and is successful in getting sober. Contrary to expectations, he actually puts an effort into maintaining his sobriety, and he tries his best to stay away from alcohol.

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While at a restaurant with Tony and Tony B., Tony tells a soda-drinking Chris to “have a f***ing drink” because he’s annoying everyone with his sobriety. It’s a horrible thing to say to someone, and it’s one of many reasons why viewers starting turning on Tony around season 5.

4 Love: “I Didn’t Hurt Nobody.”

Season 1’s “Boca” concerns Meadow’s soccer coach, Don Hauser. While everyone loves Don for his commitment to the team, Tony learns from Meadow that he has slept with teenager Ally Vandermeed. Ally, traumatized by the experience, attempts suicide. Tony wants to kill Don for sleeping with Ally, but Artie Bucco convinces him to go to the police.

Don is arrested, and a drunk Tony returns home that night, telling Carmela, “I didn’t hurt nobody.” With this, viewers learned that Tony wasn’t a complete monster (in this scenario) and thought, if only for a second, that he could be redeemed.

3 Hate: “I Haven’t Been Able To Tell Anybody This. I’m F***in’ Relieved.”

Many of the most odious Tony quotes come from his conversations with Dr. Melfi. It’s the only time that Tony can truly open up and reveal his depraved feelings. After murdering Christopher, Tony pretends that he died in the car crash and acts morosely in front of everyone to keep up the ruse.

He spills his guts to Melfi, telling her that he’s “f***in’ relieved” that Christopher is dead. It made viewers enormously sympathetic for the late Christopher, and it turned Tony into The Sopranos‘ biggest villain.

2 Love: “You’re Alright, Baby.”

Season 6 is a truly harrowing season of television, and it includes AJ Soprano’s attempted suicide. AJ ties his foot to a cinder block and jumps in the Soprano pool, but the rope proves too long and he rises to the surface. Tony returns home at an opportune time and finds his son in the backyard, jumping into the pool to save him.

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After bringing AJ out of the pool, Tony strokes his hair in a loving manner and repeats, “You’re alright, baby.” It’s one of Tony’s most loving gestures, and it proves that, despite his own admissions to Melfi, he truly does love his son.

1 Hate: “Sacre Bleu, Where Is Me Mama?”

By season 5, Tony is mostly irredeemable. The end of “Cold Cuts” sees Tony visiting his sister Janice, who has been undergoing anger management. Angry that others are bettering themselves and being happy, Tony brings up Janice’s estranged son Harpo.

He continuously mocks Janice, prompting her to become angry and throw Tony out of her house. Not only is the act itself horrific, but Tony’s obvious pride as he leaves the house has viewers fuming in frustration and hatred.

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