Robert De Niro is one of the greatest actors to ever live and the pre-eminent method actor of our generation. He has set the standard for in-depth character portrayal in high profile films, and has done so for the past 45 years. However, there is something peculiar about Bobby’s characters, they all seem obnoxious, abrasive and somewhat misogynistic; particularly his younger roles. Try to imagine him as a romantic lead – not likely. Looking through his filmography, we find many instances where our favourite protagonist portrays a complete ass. One or two can slide but over 45 years and we sort of start noticing it. We have picked five ‘bad dates’ where a few unlucky on-screen dames have had to endure his characters.

5. The Relationship with Francine (Liza Minnelli) – New York, New York. 1977

New York, New York. Martin Scorsese. 1977
New York, New York. Martin Scorsese

“Don’t ever do that again, you do not kick off the band, I kick off the band, don’t ever do it again… ever again!”.
The showbiz relationship between Jimmy Doyle and Francine Evans was the subject of Martin Scorsese’s quasi-musical flop. Jimmy is an arrogant, self-centered band leader that cannot stand anyone looking, sounding or feeling better than him in any way, shape or form. Francine’s first line to him in the opening scene was, “will you please go away”, to which he replies “no, I don’t want to”…. a few scenes later they were hitched. This sets the tone for an extremely tumultuous relationship.

4. The Marriage to Caroline (Ellen Barkin) – This Boy’s Life. 1993

This Boy's Life. Michael Caton-Jones. 1993
This Boy’s Life. Michael Caton-Jones

“I know a thing or two about a thing or two”.
Simple-minded Dwight Henson, is an insecure man with extremely low self esteem. He constantly reminds everyone that he “knows a few things about life” and retorts to confrontations with “shut your pie-hole”. Caroline, an attractive divorcee and her son, Tobias (Leonardo DiCaprio) fall for his charm initially but quickly realize just how shallow it runs. This should be a ‘double date’ because quite frankly Tobias gets the worst of this deal. The final scene is an all out melee between a very young DiCaprio and De Niro over an empty jar of mustard… “Is it empty?”

3. The Killing of Melanie (Bridget Fonda) – Jackie Brown. 1997

Jackie Brown. Quentin Tarantino. 1997
Jackie Brown. Quentin Tarantino

“Don’t say another word okay, just keep your mouth shut… I mean it, don’t say one f*cking word, okay”… *bang!
Louis and Melanie seemed to get along pretty well for most of this film. Getting high and watching girls in bikinis marketing AK-47’s. Melanie is the loose, cheerful surfer girlfriend to Ordell (Samuel L. Jackson), who offers sex to Louis like she’s offering tea. The two exist blissfully until they have to carry out a job together. Louis is tightly strung and Melanie picks the wrong day to taunt him. “Looooo-ish… Looo-isssssss, have you lost your car?”  He warns once, twice and the third sound out of him is his pistol releasing a bullet into her stomach.

2. The Abuse of Vickie (Cathy Moriarty) – Raging Bull. 1980

Raging Bull. Martin Scorsese. 1980
Raging Bull. Martin Scorsese

“That’s not what i heard… I heard things Joey, I heard things…did Salvy f*ck Vickie?”
Arguably Robert De Niro’s greatest performance. A portrayal of Middleweight boxing champion, Jake LaMotta – an abrasive, arrogant boxer. The film follows his growing paranoia with everyone around him, including, his brother, Joey (Joe Pesci), his new wife, Vickie and business associate, Salvy. His bloated ego only exacerbates the situation as his obsession grows… As she switches off to him, he becomes more controlling; speaking to her like a child and smacking her around. After hearing a rumour coupled by an off-hand comment, his paranoia reaches a climax and he goes on an onslaught, beating his brother down and landing a knockout punch to Vickie; knocking her out cold.

1. The Abandonment of Edie (Amy Brenneman) – Heat. 1995

Heat. Michael Mann. 1995
Heat. Michael Mann

“Never let yourself get attached to anything you are not willing to walk out on in thirty seconds flat… when you feel the heat around the corner”.
This was the discipline that bank robber, Neil McCauley lived by. Edie’s situation was particularly painful because she was probably the one lady that Bobby’s character genuinely fell for.  After charming the lonely graphic designer and convincing her to leave town with him to start a new life, he makes one last stop to ‘sort out’ one last thing. Except this is the stop that Lieutenant Hanna (Al Pacino) catches up with him. As he returns to the car to meet Edie, he spots Lt. Hanna approaching from a distance, he pauses, stares straight at Edie and slowly walks away, leaving her, open-mouthed and completely dumbfounded. A painful culmination to their blissful courtship.