Roger's Disguise:

Laura Vanderbooben from ‘Stanny Slickers 2: The Legend of Ollie's Gold’

Roger comes to the kitchen table and nibbles on a waffle and puts it on his plate.

After Hayley suggests Roger get a job he says I guess, the waffle vanishes until Steve sits down.
It reappears when Francine sets the hot dogs down in front of Steve.

The title of this episode is a play on words from the quote, “Now is the winter of our discontent” from William Shakespeare's play “Richard III”

During the Seattle, Washington 1994 flashback we see Roger in a coffee shop dressed in a green striped shirt and messy blond wig.

This is a reference to Kurt Cobain (1967-1994), lead singer of Nirvana and how he appeared in their video “Smells Like Teen Spirit”

Francine: “Dinner's almost ready. I'm doing one of Rachael Ray's 30 Minute Meals, but I'm saving 10 minutes by not being all fake and smiley”

Rachael Ray's (1968-) Food Network tv show, 30 Minute Meals (2001-Present) is mentioned in this episode.

Stan: “...but you strut around like you're Mary Queen of Scots, Brangelina & Jesus all rolled into one...”

Stan mentions “Brangelina”, the nickname the tabloid press gave celebrity couple Brad Pitt (1963-) & Angelina Jolie (1975-)

Roger: “I'm the decider”

This is a reference to former President George W. Bush's April 2006 quote when he was speaking about Don Rumsfeld, the full quote being, “I'm the decider, and I decide what is best. And what's best is for Don Rumsfeld to remain as the Secretary of Defense”

Stan: “Ha Ha, the Decider, what is that? Some new Lea Thompson legal thriller on Lifetime ?”

Stan mentions the Lifetime cable network & American actress Lea Thompson (1961-)

Roger: “I've decided Stan! I'm going to my Fortress of Solitude outside Roswell...”

(Obvious) Reference to Superman and his home in the North Pole as well as the July 7th, 1947 alleged flying saucer crash in Roswell, New Mexico

Disability Check Dan: “Excuse me gentleman, if I just found out I'm the Lindberg baby, whom do I tell?”
Reference to the events from 1932 when the famous aviator's son, Charles Lindberg Jr. was kidnapped and later found killed.
Also the fact that even today, hoaxers claimed to actually be the Lindberg baby.

Steve: “I'm screwed man, I can't beat a tiny Asian boy at eating hotdogs.”

This is most likely an allusion to Takeru Kobayashi.
He is a Japanese competitive eater and a member of the International Federation of Competitive Eating (IFOCE).
He held the world record for hot dog eating for 5 years in a row 2001-2006.
He came in 2nd in 2007 and once again came in first in 2008.

Roger: “Of course I know what this means, I just missed my chance to sing Who Let the Dogs Out. It would have been perfect a moment ago”

“Who Let the Dogs Out” was a song originally recorded by Anslem Douglas for “Trinidad and Tobago's Carnival season” of 1998, but made famous when it was performed by the Baha Men in 2000

Roger uses a poster of American model and actress Bo Derek (1956-) as a road map

Snot: “Don't you mean, Oh my Godzilla? THANK YOU”

The classic Japanese monster “Godzilla” is mentioned in this episode

The Animal Control officer imitates the way David Caruso (1956-) puts on his sunglasses while delivering a cheesy one-liner at the start of the CBS show “CSI: Miami” (2002-Present)