The Resume

(August 1, 1958- )
Born in Greenwich Village, NYC, New York
Oldest of the Penn brothers (includes Sean and Chris)
Albums include ‘March’ and ‘Free-for-All’
Singles include ‘No Myth’ and ‘This n’ That’
Winner of the MTV Best New Artist Award (1990)
Irish/Italian/Jewish

Why he might be annoying:

In a clear act of nepotism, Sean hosted a 1987 episode of Saturday Night Live and had him on as a musical guest.
He was a member of Doll Congress, a Los Angeles-based alternative band.
His official website’s main page is a tribute to vintage television — and a chore to enter.
Free for All, though critically acclaimed, fell off the charts as quickly as it entered.

Why he might not be annoying:

He collaborated with his future wife – Aimee Mann of ’Til Tuesday – on her own album (‘I’m With Stupid’) and later an anti-file-sharing and pro-copyright company.
He collaborated on the film score for ‘Boogie Nights’ (1997).
While he was unable to chart on the Billboard Hot 100 with ‘Brave New World’ (also from ‘March’), he managed to get a few more singles charted in Modern Rock Tracks.
He went on to have his own record label (Mimeograph Records).

Credit: Cool It All Right?

Featured in the following Annoying Collections:

• Billboard Rock Artist of the Year (Ranked: 1990)
• Celebrities Born on the Same Date [August] (Ranked: 8011958)
• Cool It All Right?'s Profiles [Series 04]
• Entertainment Weekly's It List [2000]
• Green Bagels [Irish Jews]
• I Live in My Sibling's Shadow
• I Married in 1997
• MTV VMA: Best New Artist in a Video (Ranked: 1990)
• My Song is on Rhino's 'Whatever: The 90's Pop & Culture Box'
• New Musical Express' Top Albums [1990] (Ranked: 34)
• Penn Family
• Pizza and Brew [Irish Italians]
• Pizza Bagels [Italian Jews]
• Profiles 22751-23000 (Ranked: 22968)
• Saturday Night Live Musical Guests [1985-89] (Ranked: 1987)

Year In Review:

In 2023, Out of 4 Votes: 0% Annoying
In 2022, Out of 7 Votes: 14.29% Annoying
In 2021, Out of 13 Votes: 46.15% Annoying
In 2020, Out of 3 Votes: 66.67% Annoying
In 2019, Out of 14 Votes: 14.29% Annoying
In 2018, Out of 6 Votes: 50.0% Annoying
In 2017, Out of 20 Votes: 55.00% Annoying
In 2016, Out of 3 Votes: 66.67% Annoying
In 2015, Out of 12 Votes: 41.67% Annoying
In 2014, Out of 18 Votes: 38.89% Annoying
In 2013, Out of 17 Votes: 47.06% Annoying
In 2012, Out of 21 Votes: 19.05% Annoying
In 2011, Out of 18 Votes: 27.78% Annoying
In 2010, Out of 31 Votes: 45.16% Annoying
In 2009, Out of 26 Votes: 46.15% Annoying
In 2008, Out of 45 Votes: 71.11% Annoying