I think you and I are the big Penn fans here on the board. : ) Oh, and I love that you included his stints on 'Friends' and 'Two and a Half Men,' lol.
FYC:
Since 'Up at the Villa' and 'Crackers' both have below fewer than 3k votes and aren't otherwise noteworthy, I'm wondering if replacing with the characters from the following films makes sense:
Eddie in She's So Lovely (Won Best Actor at Cannes)
https://www.imdb.com/title/tt0120112/mediaviewer/rm1371873537/?ref_=ttch_ph_3
https://www.imdb.com/title/tt0120112/mediaviewer/rm3338443008/?ref_=ttch_ph_2
Jack Holden in Licorice Pizza (he really stole his main scene; Oscar nom for Best Picture; 155k @ 7.1; 90 meta score)
https://www.imdb.com/title/tt11271038/characters/nm0000576/?ref_=ttfc_fcr_3_116
Paok, If you want another character & film to replace Risky Business, here's one from the same time period and with the same co-star as Risky Business:
FYC:
Alex Dwyer (in Taps)(Taps: 22k @ 6.8)
https://www.imdb.com/title/tt0083169/mediaviewer/rm2076837888/?ref_=ttmi_mi_5_3
https://www.imdb.com/title/tt0083169/mediaviewer/rm3318030593/?ref_=ttmi_mi_3
Hip hip hooray! Another Live Poll: https://www.imdb.com/poll/koH4VdPjHJtCWRgM45SrVg/
Congratulations, Paok.
(Please change the setting to "Praise" and mark it as a "Live Poll." Thank you!)
rubyfruit76
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