The Resume

(August 5, 1965- )
Portrayed Cyril O'Reily on HBO's 'Oz (2001-2003)'
Acted in ‘The People vs. Larry Flynt (1996),’ ‘Good Will Hunting (1997)’ and ‘Jay and Silent Bob Strike Back (2001)’
Brother of Dean Winters

Why he might be annoying:

Before becoming actors, he and Dean Winters worked as ‘brother bartenders.’
With his long girlish blond hair, he looks like a lost Nelson brother.
When not on the ‘Oz’ set, he wore his hair in cornrows.
Many ‘Oz’ fans hated his character’s storyline.

Why he might not be annoying:

On 'Oz,' he portrayed a mentally retarded character in a sensitive and tasteful way.
He had a memorable bit part in ‘Good Will Hunting.’
He lives in his brother’s shadow.
He cut his hair.

Credit: Wieland Kalligaro

Featured in the following Annoying Collections:

• 2008 - 100 Least Annoying (Ranked: 29)
• 24
• Freezing Names
• I Married in 2003
• I Portrayed a Retard
• Kevin Smith Films
• Lion Manes
• Oz
• Profiles 13751-14000 (Ranked: 13797)
• Wieland Kalligaro's Profiles [Series 5]

Year In Review:

For 2024, as of last weekly ranking, Out of 1 Votes: 100% Annoying
In 2023, Out of 11 Votes: 36.36% Annoying
In 2022, Out of 17 Votes: 5.88% Annoying
In 2021, Out of 22 Votes: 40.91% Annoying
In 2020, Out of 5 Votes: 0% Annoying
In 2019, Out of 20 Votes: 30.0% Annoying
In 2018, Out of 5 Votes: 40.0% Annoying
In 2017, Out of 23 Votes: 78.26% Annoying
In 2016, Out of 2 Votes: 50.0% Annoying
In 2015, Out of 19 Votes: 57.89% Annoying
In 2014, Out of 22 Votes: 31.82% Annoying
In 2013, Out of 61 Votes: 34.43% Annoying
In 2012, Out of 69 Votes: 49.28% Annoying
In 2011, Out of 187 Votes: 43.85% Annoying
In 2010, Out of 443 Votes: 43.79% Annoying
In 2009, Out of 1901 Votes: 35.30% Annoying
In 2008, Out of 3159 Votes: 29.00% Annoying
In 2007, Out of 69 Votes: 55.07% Annoying
In 2006, Out of 121 Votes: 50.41% Annoying
In 2005, Out of 258 Votes: 46.12% Annoying