Macy's Thanksgiving Parade Balloons Since 1927
The Macy's Thanksgiving Parade has been a tradition of Thankgiving for decades. It started out as a way for the employees of Macy's to say thank you to New York. Macy's started using balloons in their parade in 1927 and it has been tradition since. Here's part 1 featuring balloons from 1927 to 1968.

"The Macy's Thanksgiving Day Parade dates as far back as the 1920's, when Macy's employees, many of whom were immigrants, began this tradition in an attempt to connect with American culture by celebrating Thanksgiving."

Balloon years, when given, come from various sources, including Wikipedia and Macy's website itself. Some have no name or date and a guess was made as to what year they may have appeared.
This is by no means comprehensive as there are most likely many balloons, especially early on that are not included.

1927 Felix the Cat
Macy's used to release the balloons after the parade was over. Tickets were attached with a reward of $100 for the return of the balloons. That was a fairly nice reward. As an example, a cost around that time period, for a new stove could range from $30 to $60. A nice radio could cost $15 or a new ice box about $30.

Unknown Father Knickerbocker
Father Knickerbocker is a pen named used by Washington Irving, who wrote the first history of New York and was Manhattan's first best seller. The then 26-year-old, used the name Diedrich Knickerbocker, "Diedrich" meaning "father" in Dutch, and a note by Irving in the book, indicating Knickerbocker meant to nod or doze over books.

Unknown Alligator
Facts and tidbits used are also from various sources, a special thanks to David Tarkington and his blog which has some nice bits of trivia.

1932 A...turkey?

Unknown Hippo

1934 Mickey Mouse

1935 The Marx Brothers
These particular ones are from 2004.

1937 The Nantucket Sea Monster

1937 Pinocchio

1937 Christmas Stocking

1938 Acrobats

1938 Uncle Sam

1939 Santa

1939 Superman

1940 Eddie Cantor

Boardwalk Empire fans know Eddie Cantor as a character on the show. But in case you didn't know, he was based on a real person.

Unknown Ferdinand the Bull

1940 The Tin Man

1941 Fish

No parade was held during the years 1942-1944 because of war efforts and a shortage of rubber and helium.

1945 Jack-o-Lantern

1945 Harold the Clown

1946 Harold the Baseball Player

Pilgrim 1946

1947 Artie The Pirate

1947 Artie the Gnome

Unknown Clown II

1947 Harold the Police Officer

1948 Harold the Fireman

1949 Toy Soldier

1951 Daschund/Lucky Pup

1951 Mighty Mouse

1951 Flying Fish V.2

1952 Spaceman

1957 Popeye
Numerous stories report that during a rain storm, Popeye's hat filled with water. It eventually tipped over onto parade watchers. Merry Christmas!

1960 Happy Dragon
c. 1973

Also a Happy Dragon, but no date given. Obviously much older based on the cars.

Unknown Toy Soldier

1961 Bullwinkle J. Moose
Apparently the oldest balloon still in use.

1962 Donald Duck
"Heavy rain filled the brim of Donald Duck’s hat in 1962, causing the character to tip over and dump 50 gallons of water on unamused onlookers."
I'm thinking other onlookers were highly amused.

1963 Sinclair Oil Dino the Dinosaur

1964 Linus the Lionhearted

1965 Underdog

1966 Smokey Bear

1966 Superman V.2

1968 Aviator Snoopy
Part 2, tomorrow. But no promises.