Cows and Cars - Chicago, Illinois

Reuben and Mandy Visit New York

The idea behind this card is that the ridiculously dressed country bumpkins are so overwhelmed by the tall buildings in New York City that all they can do is look up. The name Reuben is not a coincidence either. The nickname for Reuben is Rube. Here's the definition from Merriam Webster:
Rube

Pronunciation: \ˈrüb\

Function: noun

Etymology: Rube, nickname for Reuben

Date: 1891

1 : an awkward unsophisticated person : rustic
2 : a naive or inexperienced person

This card is greatly enhanced by the message. The sender, undoubtedly a country bumpkin himself, seems to have relished the humor. Here's the message side of the card:

The message sent to Miss Alta Bonney in 1908, reads:

We are nearly through haying would have got done if it had not rained this week. from your friend Charlie

Madison Square, New York

Here we are at Broadway and 5th at Madison Square in New York City.  The 5th Avenue Hotel, shown on the left on both cards, had one of the world's first elevators. The cards are both prior to 1907. The first one is from 1906, since the company only printed cards in 1906 and 1907, and a 1907 card  would have had a back divided into two sections for address and message.
The 5th Avenue Hotel, built in 1859 at 200 Fifth Avenue, was demolished in 1908. The site is currently occupied by the Toy Center Building, built in 1909.

On the second card, you can still see the Fifth Ave. Hotel on the left, but you can also see the tower from Madison Square Garden off on the right. Madison Square Garden was designed by Stanford White, who was also murdered there in 1906, about the time this postcard was published. White was murdered by millionaire, Harry Kendall Thaw, over White's affair with Thaw's actress wife Evelyn Nesbitt.

Here are the backs of the cards in the same order as above: