Harley Quinn/Poison Ivy history
Harley and Ivy’s relationship first started in Batman: The Animated Series and its followup The New Batman Adventures. The main episodes featuring them together are:
There was also a webseries called Gotham Girls that features them a lot. There are some low quality videos of it on Youtube. And then they were also in one episode of Static Shock, called “Hard as Nails”. And finally the Batman and Harley Quinn movie which was.. not great.
Then there are the comics that tie-in to the animated universe:
The Batman Adventures #12 (Sep 1993) - Harley Quinn’s first comic appearance, in which they colored her mask wrong
The Batman Adventures Holiday Special #1 (Jan 1995) - the episode Holiday Knights was based on this comic
The Batman & Robin Adventures #8 (Jul 1996)
The Batgirl Adventures #1 (Feb 1998) - this is an important one
Batman: Gotham Adventures #10 (Mar 1999)
Batman: Gotham Adventures #29 (Oct 2000)
Gotham Girls (2003-2003) - miniseries
Batman Adventures #1 (Jun 2003) - start of an ongoing storyline
Batman Adventures #3 (Aug 2003)
Batman Adventures #16 (Sep 2004)
Batman: Harley & Ivy (2004) - miniseries
Batman and Harley Quinn (2017-2018) - miniseries
After Harley Quinn was successful in the animated series, they ported her over to the main comic universe, and that included her relationship with Poison Ivy. Some of their more notable appearances together are:
Batman: Harley Quinn (Oct 1999)
Arkham Asylum: Madness (2000)
Joker/Mask (2000) - crossover miniseries
Harley Quinn (2000-2004) - series, Poison Ivy is in it up until issue 19
Batman: Gotham Knights #14 (Apr 2001) - backup story
Harley and Ivy: Love on the Lam (2001)
Gotham City Sirens (2009-2011) - series
Batman: Black and White #3 (Jan 2014) - the story “Role Models”
Harley Quinn (2014-ongoing) - series, Poison Ivy is a recurring secondary character
Batman #42-#43 (2018) - the “Everyone Loves Ivy” story arc, leading into Heroes in Crisis
Heroes in Crisis (2018-2019) - miniseries
Harley Quinn and Poison Ivy (2019-ongoing) - miniseries, spinoff from Heroes in Crisis
Harley and Ivy also show up in alternate universes like Injustice and DC Comics Bombshells. Both of those have ensemble casts and it can be a long time between appearances.
This isn’t everything but I’m pretty sure it’s all the important things.
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