diff --git a/beets/dbcore/types.py b/beets/dbcore/types.py
index 1b8434a0b..f03731a55 100644
--- a/beets/dbcore/types.py
+++ b/beets/dbcore/types.py
@@ -18,9 +18,19 @@ from __future__ import annotations
 
 import re
 import time
+from types import GenericAlias
 import typing
 from abc import ABC
-from typing import TYPE_CHECKING, Any, Generic, TypeVar, cast
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Generic,
+    TypeVar,
+    cast,
+    get_args,
+    get_origin,
+    get_type_hints,
+)
 
 import beets
 from beets import util
@@ -454,6 +464,58 @@ class DurationType(Float):
                 return self.null
 
 
+def get_type_parameters(instance: Type) -> tuple[type, type]:
+    """
+    Extract T and N types from a Type instance.
+
+    Returns:
+        Tuple of (T_type, N_type) or (object, object) if cannot determine
+    """
+    n_type: type
+    t_type: type
+    try:
+        # Get T type from model_type attribute or default to object
+        t_type = getattr(instance, "model_type", object)
+
+        if hasattr(t_type, "__origin__") and get_origin(t_type) is not None:
+            # This is already a generic type, keep it as-is
+            pass
+        else:
+            # For non-generic types, ensure we have the actual type
+            t_type = type(t_type) if not isinstance(t_type, type) else t_type
+
+        # Get N type from null attribute with proper handling
+        if hasattr(instance, "null"):
+            null_value = instance.null
+            if null_value is None:
+                n_type = type(None)
+            else:
+                n_type = type(null_value)
+                # For generic types in null values, try to infer from class definition
+                if isinstance(null_value, list) and hasattr(
+                    instance.__class__, "__orig_bases__"
+                ):
+                    # Try to extract the generic type from class inheritance
+                    for base in getattr(
+                        instance.__class__, "__orig_bases__", []
+                    ):
+                        if get_origin(base) is not None:
+                            base_args = get_args(base)
+                            if len(base_args) >= 2 and base_args[1] is not Any:
+                                n_type = base_args[1]
+                                break
+        else:
+            # Default N type is the same as T for non-nullable types
+            n_type = t_type
+
+        return t_type, n_type
+    except (AttributeError, TypeError):
+        pass
+
+    # Final fallback: return object types
+    return object, object
+
+
 # Shared instances of common types.
 DEFAULT = Default()
 INTEGER = Integer()
diff --git a/scripts/generate_model_stubs.py b/scripts/generate_model_stubs.py
new file mode 100644
index 000000000..aa8702878
--- /dev/null
+++ b/scripts/generate_model_stubs.py
@@ -0,0 +1,169 @@
+"""
+We found that using the beets library models can sometimes be frustrating because of
+missing typehints for the model attributes and methods.
+
+This script does the following in order:
+- generates or overwrite the current models.pyi stub files.
+- injects type hints for the __getitem__ method depending on the defined fields
+"""
+
+from __future__ import annotations
+
+import logging
+import re
+import subprocess
+from pathlib import Path
+from typing import Union, get_args, get_origin
+
+from beets.dbcore.types import get_type_parameters
+from beets.library import Album, Item, LibModel
+
+log = logging.getLogger(__name__)
+
+
+def overload_template(key: str, return_type: type) -> list[str]:
+    """Generate an overload for __getitem__ with a specific key and return type."""
+    type_str = type2str(return_type)
+    return [
+        "@overload",
+        f"def __getitem__(self, key: {key}) -> {type_str}: ...",
+    ]
+
+
+def type2str(tp: type) -> str:
+    """Convert a Python type into a PEP 604 style string for stubs."""
+    # Handle NoneType first since it doesn't have __name__
+    if tp is None or tp is type(None):
+        return "None"
+    if tp is object:
+        return "Any"
+
+    origin = get_origin(tp)
+    if origin is None:
+        # It's a simple type
+        return tp.__name__
+    elif hasattr(origin, "__name__"):
+        # It's a regular generic type like list, dict, etc.
+        args = get_args(tp)
+        if args:
+            args_str = ", ".join(type2str(arg) for arg in args)
+            return f"{origin.__name__}[{args_str}]"
+        else:
+            return origin.__name__
+    else:
+        # Handle special forms like Union, Optional, etc.
+        args = get_args(tp)
+        if origin is Union:
+            return " | ".join(type2str(arg) for arg in args)
+        else:
+            # For other special forms, fall back to string representation
+            return str(tp)
+
+
+def generate_overloads(model: type[LibModel]) -> list[str]:
+    """Generate overloads for __getitem__ based on Item._fields."""
+    lines: list[str] = []
+    count = 0
+    for name, field_type in model._fields.items():
+        return_type, null_type = get_type_parameters(field_type)
+        lines.extend(
+            overload_template(
+                f"Literal['{name}']", Union[return_type, null_type]
+            )
+        )
+        count += 1
+
+    # Default str
+    lines.extend(overload_template("str", object))
+
+    log.info(f"Generated {count} overloads for {model.__name__}")
+    return lines
+
+
+def inject_overloads(stub_path: Path, model: type[LibModel]) -> None:
+    """Insert generated overloads into the class definition in a .pyi file."""
+    text = stub_path.read_text()
+
+    class_name = model.__name__
+    log.info(f"Injecting overloads for {class_name} into {stub_path}")
+
+    # Find the class definition
+    class_pattern = rf"^(class {class_name}\(.*\):)"
+    match = re.search(class_pattern, text, flags=re.MULTILINE)
+    if not match:
+        raise RuntimeError(f"Class {class_name} not found in {stub_path}")
+
+    # Where to insert
+    insert_pos = match.end()
+
+    # Prepare overload block and indent
+    overloads = generate_overloads(model)
+    overload_text = "\n".join(f"    {line}" for line in overloads)
+
+    # Insert after class line
+    new_text = text[:insert_pos] + "\n" + overload_text + text[insert_pos:]
+
+    # Write result
+    stub_path.write_text(new_text)
+    log.info(f"Injected overloads into {stub_path}")
+
+
+def run_stubgen(module: str, out_dir: Path) -> Path:
+    """Run stubgen for a module and return the generated pyi path."""
+    subprocess.run(
+        ["stubgen", "-m", module, "--include-private", "-o", str(out_dir)],
+        check=True,
+    )
+    # Figure out the generated file path
+    pyi_path = out_dir / Path(module.replace(".", "/") + ".pyi")
+    if not pyi_path.exists():
+        raise FileNotFoundError(f"Stubgen did not generate {pyi_path}")
+    return pyi_path
+
+
+def format_file(stub_path: Path) -> None:
+    """Run ruff fix on the generated stub file."""
+    subprocess.run(
+        [
+            "ruff",
+            "check",
+            str(stub_path),
+            "--fix",
+            "--unsafe-fixes",
+            "--silent",
+        ],
+        check=True,
+    )
+
+
+def ensure_imports(stub_path: Path) -> None:
+    """Ensure multiple imports are present in the generated stub file."""
+    text = stub_path.read_text()
+
+    if "from typing import Literal" not in text:
+        insert_pos = text.find(
+            "from typing"
+        )  # Attempt to find the first typing import
+        if insert_pos == -1:
+            # No existing import, add at the top of the file
+            insert_pos = 0
+        else:
+            # Otherwise, find the position after the first import line
+            insert_pos = text.find("\n", insert_pos) + 1
+
+        # Add Literal import
+        new_text = (
+            text[:insert_pos]
+            + "from typing import Literal, Any, overload\n"
+            + text[insert_pos:]
+        )
+        stub_path.write_text(new_text)
+
+
+if __name__ == "__main__":
+    logging.basicConfig(level=logging.INFO)
+    out_dir = Path(__file__).parent.parent
+    file = run_stubgen("beets.library.models", out_dir)
+    ensure_imports(file)
+    inject_overloads(file, Item)
+    inject_overloads(file, Album)
diff --git a/test/test_types.py b/test/test_types.py
index 6727917d8..457f5297f 100644
--- a/test/test_types.py
+++ b/test/test_types.py
@@ -1,4 +1,7 @@
 import time
+from tkinter import N
+
+import pytest
 
 import beets
 from beets.dbcore import types
@@ -56,3 +59,34 @@ def test_durationtype():
     beets.config["format_raw_length"] = True
     assert 61.23 == t.format(61.23)
     assert 3601.23 == t.format(3601.23)
+
+
+@pytest.mark.parametrize(
+    "type, type_params",
+    [
+        (types.DEFAULT, (str, type(None))),
+        # ints
+        (types.Integer(), (int, int)),
+        (types.NullInteger(), (int, type(None))),
+        (types.PaddedInt(2), (int, int)),
+        (types.NullPaddedInt(3), (int, type(None))),
+        (types.ScaledInt(2, "foo"), (int, int)),
+        (types.Id(), (int, type(None))),
+        # floats
+        (types.Float(), (float, float)),
+        (types.NullFloat(), (float, type(None))),
+        (types.DateType(), (float, float)),
+        (types.DurationType(), (float, float)),
+        # Strings
+        (types.String(), (str, str)),
+        (types.DelimitedString(","), (list[str], list[str])),
+        (types.MusicalKey(), (str, type(None))),
+        # Other
+        (types.Boolean(), (bool, bool)),
+        # Paths
+        (types.PathType(), (bytes, bytes)),
+        (types.NullPathType(), (bytes, type(None))),
+    ],
+)
+def test_get_type_parameters(type: types.Type, type_params):
+    assert type_params == types.get_type_parameters(type)