From May 9-12, 2006, Conan O'Brien embarked on his first trip out of 30 Rock in New York since the historic visit to Toronto in 2004, headed for a week's worth of shows from the historic Chicago Theater in Chicago. With a great lineup including Dave Chappelle and Sean Hayes, the shows were destined to be a surefire hit. However, observant (and rather sad) viewers like myself noticed a lot of elements that made Conan's Toronto visit so special evident in Chicago as well, presenting the evidence here for you to determine whether or not Conan's Chicago trip really was just an homage to Conan's week in Canada, simply re-hashing used pieces, simply because Conan's visit to Toronto never can, and never will, be outdone.

First we have The Masturbating Bear...originally unscheduled, not to mention banned, from Chicago, the Bear made a dramatic Mission Impossible-esque entrance, skydiving onto the shores of the Chicago River, and then making an entrance at the Chicago Theatre, much to Conan's dismay. However, the Bear was no stranger to making entrances from high above ground, as the Bear took to the skies in Toronto's financial district on February 11, 2004, appearing from a high-rise to appear on a Conan-ized version of Toronto.com. Not a huge ripoff of Conan in Toronto, but it signaled the start of much more to come...
 
Every night in Chicago before the first guest joined Conan onstage, Conan and bandleader Max Weinberg engaged in stirring renditions of a "Late Night Chicago Small Talk Moment". A now common-staple of Late Night, Conan and Max debated about issues like the Chicago mayoral election and subway system, similar to other non-sensical rants on the show. However, many may forget that the Small Talk Moments made their debut in Toronto, as the historic Canadian Small Talk Moments set the standards for years to come. Plus, Conan and Max didn't even dress up this time!
 
While not a clearly visible part of the shows, yet another strange development that echoed Conan's Toronto visit, as with the exception of Vlasta the Polka Queen, who was not even an actual guest of Conan's, there were no female guests on the entire week in Chicago! Even though the area is home to such well-known ladies as Jenny McCarthy, Virginia Madsen, Robin Tunney...hell, even Oprah Winfrey (!), and musicians like Liz Phair and Veruca Salt, there was not a single female guest of Conan's the entire week, echoing the total lack of estrogen during Conan's visit to Toronto...let's just hope that next time Conan will bring some of the ladies along for the ride!
 
Conan's first guest on his Chicago trip proved to be a constant reminder of Toronto in more ways than one, as Sean Hayes made an appearance to mark the final week of Will & Grace's tremendous eight year run. However, it was not the first time Conan turned to a Will & Grace alumnus to promote an out-of-town visit, as Hayes' co-star Eric McCormack appeared on the February 13, 2004 edition of Late Night in Toronto. On a sidenote, Hayes' dramatic musical entrance was eerily similar to Jim Carrey's stirring rendition of "A Place To Stand," performed with Conan just before McCormack's appearance.
 
Promoting local stars such as Sean Hayes, John C. Reilly, Cheap Trick, Wilco and Common, it was quite a surprise to see that perhaps the biggest draw of the week was comedian Dave Chappelle. Chappelle, who is certainly no stranger to the Windy City, and has many ties to the city, is in fact a native of Washington, D.C., and currently resides in rural Ohio. This "white elephant" of sorts is similar to Adam Sandler's inclusion in Toronto on February 12, 2004, as Sandler is a native of New Hampshire, nowhere close to being Canadian. Perhaps the only difference is that Chappelle, unlike Sandler, did not try to argue that he was in fact from the host city.
 
Brought in to provide an authentic (and largely unintelligble) Chicago polka flavour, Vlasta, the self-proclaimed International Queen of Polka, appeared on Late Night to serenade the Chicago Theater crowd, as well as a very lively Conan O'Brien, with a special polka composed to commemorate the historic visit. However, this was not the first time Conan recruited a qwirky local to appease the hometown crowd, while surely confusing outside viewers, as international moose calling champion Ken Capling appeared in Toronto on February 11, 2004, generating huge laughs from the Canadian crowd, but surely alienating most of Conan's American viewers.
 
To conclude his interview, actor John C. Reilly brought his hometown Chicago crowd to their feet when he and Conan performed a stirring rendition of Paper Lace's "The Night Chicago Died," to a roused and energetic audience. However, Conan is no stranger to belting out a tune to impress the locals when on the road, as Jim Carrey put Conan to the Canadian test on February 13, 2004, when he started (AND finished) his interview with great performances of Dolores Claman's "A Place To Stand," considered the unofficial theme song of the province of Ontario, to a booming Toronto audience, who gladly helped Conan through by singing along the entire song.
 
During Conan's desk drive with former sidekick and suburban Chicago native Andy Richter, Conan and Andy encountered a "frat" party at the University of Chicago, a trip to Wrigley Field, and much more, but perhaps the most amusing part of the trip was a stop by the bar Sidetrack, located at 3349 North Halsted St. in the Boystown section of Chicago, where Andy introduced "Consie" to the residents of the largest gay community in Chicago. However, this skit was eerily similar to Conan's tour of Toronto with Scott Thompson on February 11, 2004, where Conan was unsuspectingly brought to Woody's & Sailor in Toronto's gay district to meet the regulars.
 
While surely no visit to Chicago is complete without a visit to the famed Sears Tower, Conan decided to take it a step further, introducing his newwst character, the Sears Tower Wearing Sears Clothing, throughout the week, even having the tower crowd-surfed through the Chicago Theater. However, many will remember that Conan made his first successful attempt at patronizing national landmarks in Toronto, when he had Toronto's famed CN Tower square off in a series of challenges against the Seattle Space Needle for national tower bragging rights. Even so, this dispute could still be settled between the CN and Sears Tower in the future, with the CN Tower and its 364 ft. advantage over "measly" 1451-foot Sears Tower likely to lead to an incredibly easy beatdown victory for Canada.
 
Finally, in what many would consider the highlight of Conan's visit, Conan announced he toured the Windy City with a local native of the city, who was revealed to be the one and only Mr. T, who took Conan to his south-side neighbourhood, the Sears Tower, Comiskey Park to try out with the White Sox, before concluding with a romantic canoe ride down the Chicago River. However, fans of Conan's may remember him taking a tour of Toronto with another individual named Mr. T...Mr. Thompson, as in Scott, that is, on February 11, 2004. And Conan's antics with a pro sports team was nothing new, as Conan was certainly more creative (and irritating) towards the Toronto Maple Leafs on February 10 than he was with Jermaine Dye...and Conan didn't even get beat up this time!
 
This is not to imply, however, that the week in Chicago was a bad week of shows by any means...Dave Chappelle's appearance was hilarious, new features like the Wheel of Wendt and Joel visiting famous movie sites was classic, and as for La Bamba as the Empire Carpet Guy...absolutely legendary. Just a few simple, yet not immediately noticeable, comparisons for you to chew on...perhaps we'll see similar when Conan ventures out of NYC once again in the future, whether it be to a new locale, such as Las Vegas, Orlando or Boston...or perhaps he'll just come to his senses and return to Toronto, the site of perhaps the most solid week of Late Night from start to finish in the show's history...yes, that's right, I said it.