diff --git a/src/annotation.rs b/src/annotation.rs
index 93f976e..6a0ebc7 100644
--- a/src/annotation.rs
+++ b/src/annotation.rs
@@ -63,15 +63,21 @@ impl PyAnnotation {
         self.map(|annotation| Ok(annotation.id() == Some(other)))
     }
 
-    fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> Py<PyAny> {
-        let py = other.py();
+    fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> bool {
         match op {
-            CompareOp::Eq => (self.handle == other.handle).into_py(py),
-            CompareOp::Ne => (self.handle != other.handle).into_py(py),
-            _ => py.NotImplemented(),
+            CompareOp::Eq => self.handle == other.handle,
+            CompareOp::Ne => self.handle != other.handle,
+            CompareOp::Lt => self.handle < other.handle,
+            CompareOp::Gt => self.handle > other.handle,
+            CompareOp::Le => self.handle <= other.handle,
+            CompareOp::Ge => self.handle >= other.handle,
         }
     }
 
+    fn __hash__(&self) -> usize {
+        self.handle.as_usize()
+    }
+
     /// Returns a generator over all data in this annotation
     fn __iter__(&self) -> PyResult<PyDataIter> {
         Ok(PyDataIter {
diff --git a/src/annotationdata.rs b/src/annotationdata.rs
index eaf429d..9b6ee27 100644
--- a/src/annotationdata.rs
+++ b/src/annotationdata.rs
@@ -2,6 +2,7 @@ use pyo3::exceptions::{PyRuntimeError, PyValueError};
 use pyo3::prelude::*;
 use pyo3::pyclass::CompareOp;
 use pyo3::types::*;
+use std::hash::{Hash, Hasher};
 use std::ops::FnOnce;
 use std::sync::{Arc, RwLock};
 
@@ -66,12 +67,19 @@ impl PyDataKey {
     fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> Py<PyAny> {
         let py = other.py();
         match op {
-            CompareOp::Eq => (self.handle == other.handle).into_py(py),
-            CompareOp::Ne => (self.handle != other.handle).into_py(py),
+            CompareOp::Eq => (self.set == other.set && self.handle == other.handle).into_py(py),
+            CompareOp::Ne => (self.set != other.set || self.handle != other.handle).into_py(py),
             _ => py.NotImplemented(),
         }
     }
 
+    fn __hash__(&self) -> u64 {
+        let mut hasher = std::collections::hash_map::DefaultHasher::new();
+        let h = (self.set.as_usize(), self.handle.as_usize());
+        h.hash(&mut hasher);
+        hasher.finish()
+    }
+
     /// Returns the AnnotationDataSet this key is part of
     fn dataset(&self) -> PyResult<PyAnnotationDataSet> {
         Ok(PyAnnotationDataSet {
@@ -424,12 +432,19 @@ impl PyAnnotationData {
     fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> Py<PyAny> {
         let py = other.py();
         match op {
-            CompareOp::Eq => (self.handle == other.handle).into_py(py),
-            CompareOp::Ne => (self.handle != other.handle).into_py(py),
+            CompareOp::Eq => (self.set == other.set && self.handle == other.handle).into_py(py),
+            CompareOp::Ne => (self.set != other.set || self.handle != other.handle).into_py(py),
             _ => py.NotImplemented(),
         }
     }
 
+    fn __hash__(&self) -> u64 {
+        let mut hasher = std::collections::hash_map::DefaultHasher::new();
+        let h = (self.set.as_usize(), self.handle.as_usize());
+        h.hash(&mut hasher);
+        hasher.finish()
+    }
+
     /// Returns the AnnotationDataSet this data is part of
     fn annotationset(&self) -> PyResult<PyAnnotationDataSet> {
         Ok(PyAnnotationDataSet::new(self.set, &self.store))
diff --git a/src/annotationdataset.rs b/src/annotationdataset.rs
index c94af92..4295723 100644
--- a/src/annotationdataset.rs
+++ b/src/annotationdataset.rs
@@ -55,15 +55,21 @@ impl PyAnnotationDataSet {
         self.map(|annotationset| Ok(annotationset.id() == Some(other)))
     }
 
-    fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> Py<PyAny> {
-        let py = other.py();
+    fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> bool {
         match op {
-            CompareOp::Eq => (self.handle == other.handle).into_py(py),
-            CompareOp::Ne => (self.handle != other.handle).into_py(py),
-            _ => py.NotImplemented(),
+            CompareOp::Eq => self.handle == other.handle,
+            CompareOp::Ne => self.handle != other.handle,
+            CompareOp::Lt => self.handle < other.handle,
+            CompareOp::Gt => self.handle > other.handle,
+            CompareOp::Le => self.handle <= other.handle,
+            CompareOp::Ge => self.handle >= other.handle,
         }
     }
 
+    fn __hash__(&self) -> usize {
+        self.handle.as_usize()
+    }
+
     /// Save the annotation dataset to a STAM JSON file
     fn to_json_file(&self, filename: &str) -> PyResult<()> {
         self.map(|annotationset| {
diff --git a/src/resources.rs b/src/resources.rs
index efa4c3b..c0a1429 100644
--- a/src/resources.rs
+++ b/src/resources.rs
@@ -56,15 +56,21 @@ impl PyTextResource {
         self.map(|res| Ok(res.id() == Some(other)))
     }
 
-    fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> Py<PyAny> {
-        let py = other.py();
+    fn __richcmp__(&self, other: PyRef<Self>, op: CompareOp) -> bool {
         match op {
-            CompareOp::Eq => (self.handle == other.handle).into_py(py),
-            CompareOp::Ne => (self.handle != other.handle).into_py(py),
-            _ => py.NotImplemented(),
+            CompareOp::Eq => self.handle == other.handle,
+            CompareOp::Ne => self.handle != other.handle,
+            CompareOp::Lt => self.handle < other.handle,
+            CompareOp::Gt => self.handle > other.handle,
+            CompareOp::Le => self.handle <= other.handle,
+            CompareOp::Ge => self.handle >= other.handle,
         }
     }
 
+    fn __hash__(&self) -> usize {
+        self.handle.as_usize()
+    }
+
     /// Returns the full text of the resource (by value, aka a copy)
     fn __str__<'py>(&self, py: Python<'py>) -> PyResult<&'py PyString> {
         self.text(py)
diff --git a/src/textselection.rs b/src/textselection.rs
index 6f94a57..9b343ce 100644
--- a/src/textselection.rs
+++ b/src/textselection.rs
@@ -2,6 +2,7 @@ use pyo3::exceptions::PyRuntimeError;
 use pyo3::prelude::*;
 use pyo3::pyclass::CompareOp;
 use pyo3::types::*;
+use std::hash::{Hash, Hasher};
 use std::ops::FnOnce;
 use std::sync::{Arc, RwLock};
 
@@ -108,6 +109,13 @@ impl PyTextSelection {
         }
     }
 
+    fn __hash__(&self) -> u64 {
+        let mut hasher = std::collections::hash_map::DefaultHasher::new();
+        let h = (self.resource_handle.as_usize(), self.textselection);
+        h.hash(&mut hasher);
+        hasher.finish()
+    }
+
     /// Returns the resource this textselections points at
     fn resource(&self) -> PyResult<PyTextResource> {
         Ok(PyTextResource {